Trip with My Sugar Daddy Ch. 01

I couldn't believe what I was doing. My semester had just ended, and I was on a plane to Miami with a man I had only known for a few weeks. I should have been on a plane to see my family or making plans to find work for the break. But there was no one else I wanted to be with, and for the first time in a long time, I didn't have to worry about money.

"Are you okay?"

James' question snapped me out of my thoughts. I turned to face him and smiled, "Yes, all good. Just a nervous flier I guess."

James pulled up the armrest between us, put one arm around my neck, and rested his other hand on my leg. "Nothing to be nervous about, Laura. Just a bit of turbulence."

I smiled and leaned back against his chest, closing my eyes to try to relax. It wasn't long before I felt James' hand start to move on my leg. Each time he rubbed up and down, his hand found its way just a bit farther under my dress. Meanwhile, his other hand started stroking down my neck, slowly inching toward my chest.

Even though I had spent a good bit of time with James over the last few weeks, I still wasn't used to a man this bold. I was surprised by how much it turned me on. I never thought I'd be the type to let a man do whatever he wanted--wherever he wanted--to me like this. But here I was, uncrossing my legs for him as his hand disappeared beneath my dress.

My eyes were still closed, and I was trying to steady my breathing as his fingers inched higher. I was getting very wet with anticipation. Totally focused on what James was doing to me, I almost jumped out of my seat when I heard the flight attendant stop by our row and ask, "Can I get anything for the two of you?"

James, unfazed by our audience, smiled up at the attendant, leaving his hand well up my dress. "We're good. Thanks, sweetheart." His fingers continued to stroke my neck.

The flight attendant's eyes lingered on my leg, and then she smiled and moved to the next row, acting like nothing was happening. Maybe this sort of thing happens a lot in first class? I wouldn't know.

James leaned over and softly kissed my neck as his fingers found my pussy. I inhaled sharply as he started stroking. Meanwhile, his other hand finally slid into the top of my dress.

"I see you dressed how I like," he whispered in my ear, his fingers sliding over the top of my breast. I felt the strap of my dress fall off my shoulder.

"Of course," I answered, trying not to moan. When I was getting ready to leave earlier that day, I decided to wear a short sundress--nothing underneath. I knew James would eventually discover that I wasn't wearing a bra or panties, and that he would be pleased when he did.

"Oh God," I whispered as I felt James' fingers slide up into me while his other hand started pulling on my nipple. He curled his fingers, stroking my g spot. I bit my lip as my muscles started to tense up.

It was the middle of the day--anyone who happened to look over at us could see what was happening. But I didn't care. In fact, that only made what he was doing to me even more exciting. I moaned softly as I came.

"Good girl." James pulled his hand out from under my dress and licked his fingers. Then he smiled at me as he pulled my dress strap back up. "Hopefully that helped relax your nerves."

--

I met James by chance about a month ago. I was out at a bar with some of my friends. We were all graduate students at a local university. I had just finished a paper and decided to join them for a celebratory drink. But I was broke and realized after two drinks that I better stop if I wanted to be able to pay my rent that month. So I went up to the bar to close my tab. It was still relatively early, and the bartender asked, "Leaving so soon?"

"Yeah, I better call it a night while I can still afford to."

As I was signing the check, I noticed that the man sitting on the barstool next to me was watching me. I looked up, and he smiled at me. He was with a few other men, and they must have come from a business meeting or something because they were all wearing suits. I guessed he was 15 years or so older than me--somewhere around 40. But he was extremely good looking--tan skin, dark hair, great smile. I couldn't help but smile back.

"If I buy you a drink, will you stay a little longer?" he asked. I'm generally not one to turn down a free drink, especially from a man like him.

"I could be convinced," I said teasingly.

He motioned for me to sit down on the stool beside him as he called over the bartender.

I sat down, suddenly aware of what I must look like. I had a decent body--5'4", toned, 34C--but I was not doing myself any favors this evening. I had come to the bar in a t-shirt and jeans, my light brown hair in a messy bun and my eyes tired from writing all day. This was a man who was probably used to women in cocktail dresses, and here I was looking like I just rolled out of bed.

"What are you having?"

I saw James was drinking what I assumed was very good whiskey on the rocks. I also noticed he had a ring on his left hand. But what was the harm in having a drink? "I'll have what he's having."

The bartender got my drink, and James held his glass out, "Cheers." We clinked glasses, and I took a sip. "I'm James, by the way."

"Laura. Thanks for the drink. It's delicious."

"Thanks for the company." James looked at me like I was the most attractive woman in the place. We ended up talking and drinking for the next hour. He was extremely charming.

At one point, James' associates stood up to leave. He turned to me and said, "I hate to do this, but I have to get going. Can you get home okay?"

I was a bit surprised. I thought he was going to try to get me to a hotel or something. And I'm not sure I would have said no--ring or not. I nodded over to where my friends were. "Yes, I can head back with my friends. Thanks for the drinks."

James stood up and leaned over me, his body pressed against mine. Despite all the flirting, it was the first time he touched me all night. I felt my heart start to beat a little faster. "You know, if you ever need someone to foot your bill, feel free to give me a call." He handed me a business card as he put his mouth right by my ear and said, "I think we could have a mutually beneficial arrangement."

I didn't believe what I was hearing. Was this married man actually offering to be my sugar daddy?

Before I could say anything, he stood up and said, "Great to meet you, Laura," and walked away.

I looked down at the business card: "James Davidson, CEO, Radian Networks."

--

The next few days came and went. My interaction with James came to mind from time to time, but I was super busy and didn't have a lot of time to think about it.

Then I had to pay my bills. After everything was paid, my bank account was pretty much drained. I opened my desk drawer and saw James' card.

I knew I should be offended. The man basically offered me money in exchange for sex. And he was married. At the same time, I really did enjoy talking to him. And I found him very attractive. Would it be any different than casually dating a wealthy man who just happened to be generous? Plus, his complete honesty about the "mutually beneficial" situation was kind of refreshing. I wouldn't be guessing about the future of our relationship--it would just be what it was. And I definitely could use the financial help.

Before I could think about what I was doing, I picked up my phone and dialed his number. His voicemail kicked in. "Hi James, it's Laura. We met at the bar the other night..."

--

James called me back later that day, and we made plans to meet for dinner the next evening.

I didn't have time to go shopping, so I had to make due with what I had in my closet. I decided on a black cocktail dress and heels. I wasn't sure where this evening was going, but just in case, I put on one of my sexiest bra and panty sets--very sheer black lace. I was more nervous than I expected to be, but I knew I looked good, definitely better than I did the first time we met.

When I got to the restaurant, James was waiting near the door, looking very good in a perfectly fitted navy suit. His white dress shirt underneath had a few buttons undone. It was the look of a man who knew how to look good without trying very hard. "Laura, perfect timing. They're getting the table ready." He leaned in and kissed my cheek. "You look stunning." My heart was already beating quickly.

Once we were seated, James ordered us a bottle of wine, and we ordered our food. When the waiter left the table, he said, "To be honest, I wasn't expecting to hear from you, Laura. You're not the typical kind of girl for these kinds of," he paused before finishing his thought, "arrangements. You seem very intelligent. Very independent."

I hesitated, then figured I may as well be honest, "I didn't expect to call either. But the more I thought about it, the more the arrangement seemed to, um, make sense. Plus, spending more time with you didn't sound half bad either." I smiled up at him, looking him in the eyes.

James moved his chair closer to mine. "I was very glad to hear from you." He put his hand on my face, pulled me closer to him, and kissed me. It was a small kiss. But when he pulled back, he kept his face close and looked me in the eyes. Seeing no resistance from me, he leaned in to kiss me again, this time his tongue finding its way into my mouth.

I had never kissed someone like this so publicly. Sure, I made out with high school boyfriends in dark movie theaters and with drunk boys at college parties, but never in the middle of a high-end restaurant. But James didn't seem to care who saw us. It was the first time I learned that he would take what he wanted, when he wanted--and it definitely wouldn't be the last.

We heard someone clear their throat and pulled apart. It was the waiter with the food. James slid his chair back over, and we started eating. I was surprised at how easy the conversation was with him. During a pause in the conversation, I decided I better get some details about the arrangement. "So, how will this"--I pointed to him and then me--"work, exactly?"

James put down his fork. "Well, I'll help you with your expenses. And in exchange, you'll keep me company." He said "company" with an inflection that made it very clear what he meant. "You can prioritize your studies, of course. But otherwise, I'll expect you to join me when I'd like you to." He paused for a moment and said, "You can end the arrangement whenever you'd like. But I promise to make it fun for you, too," and smiled.

I smiled back, "I think I can do that." I needed to ask one more thing. "But what about that?" as I nodded down to the ring on his hand. Part of me had been hoping he was at least separated from his wife.

James hesitated to answer, then said, "It's nothing you need to concern yourself with." I raised my eyebrow, waiting for more of an explanation. He continued, "My marriage is really just one of convenience--my wife and I barely spend time together. She does her thing, and I do mine. But I find that my arrangements keep things simpler. They keep things separated. If this bothers you and you want to change your mind, I understand."

I thought about it for a moment. I knew this whole situation was morally questionable to begin with, and now there was definitely a wife involved. But James already had some sort of power over me--I was captivated. "No, I don't want to change my mind."

James smiled, "Good."

--

After the meal, we walked outside. James nodded to a hotel within view, "I have a room across the street." He put his hand on my lower back as we started walking in that direction.

I was a little taken aback--he didn't ask if I wanted to come back with him. He just assumed I would. But then I realized this was exactly what I had just agreed to. This wasn't a typical dating experience. James did not need to wine and dine me. I was his as long as our arrangement stood.

We walked into the hotel lobby and the concierge greeted us, "Hello, Mr. Davidson." James said hello back as he guided me to the elevator.

As soon as the elevator doors closed, he pulled me into him and started kissing my neck. His hand moved down my back and over my ass. "You look amazing, Laura."

"So do you," I leaned up and kissed him, my hands wrapped around his neck as his explored my body. When the elevator doors opened, he took my hand and led me down the hall to his suite.

Once we were in the room, James took off his jacket and poured us wine. He handed me mine, and then he sat down on the couch. Before I could sit beside him, he said, "Come stand in front of me and turn around."

I took a sip of wine, set the glass down, and did as I was told. I felt his hand come up my back to my zipper and slowly pull it down. "Now face me."

I turned around and looked in his eyes. They were heavy with lust. I knew what he wanted. I slid my dress off and let it fall to the floor. He took his time looking at me in my bra and panties. I don't think a man had ever just sat and looked at me like that. I felt exposed. And so turned on. "Now everything."

Without hesitation, I reached back and unclasped my bra, letting it fall to the floor. Then I looped my fingers in my panties and pulled them down, kicking them to the side. All I had on were my heels. Part of me felt like such a slut, stripping in front of a married man, making myself completely available to him. But the situation made me wet with excitement.

James let out a soft groan as he watched me, and I saw the outline of his cock through his pants. I had never wanted anything so much. I got on my knees and unbuttoned his shirt, pulling it open to reveal a well-toned chest. Then I undid his belt and pants. His hand was fondling my breast as I undressed him. He was gentle at first, his thumb running over my hard nipple, and then he got a little rougher, grabbing the entire thing and massaging deeply.

I pulled his cock out of his pants and stroked it as I looked up at him. He let go of my breast and slid his pants completely off. I leaned over and started licking up and down. It was long and thick. I wrapped my lips around it and took it deep into my mouth.

I never wanted to please a man as much as I did at that moment. I slid his cock in deep until it hit my throat, then held it there a moment before starting to move it in and out of my mouth. At one point he pulled my hair back with his hand and held it, watching me as I continued to work his cock.

James finally let go of my hair. I felt his hand come to my chin, lifting my head. His cock slid out of my mouth, saliva stringing between it and my lips. He leaned forward and kissed me as he pulled me on top of him, straddling him. "Fuck, Laura." My pussy came into contact with his cock, and it was dripping.

He kissed down my neck and to my breasts, taking a nipple into his mouth, sucking at first, then biting softly. "Oh," I moaned as I felt his teeth. He grabbed my ass with his other hand as he continued to suck my nipple. I rocked my hips, my wet pussy sliding over his cock.

I felt his mouth move off my breast as he lifted his head. He put his other arm around my ass and stood, lifting me up and carrying me to the bed. His hard cock was still right against my pussy. I could hardly stand it anymore--I needed him inside me.

He kissed me deeply before putting me down on the edge of the bed. He stood between my legs, took his cock in his hands, and slid it right into me. "Oh God, James," I moaned. He grabbed one of my ankles and started thrusting.

I had been so turned on this entire evening that it didn't take long for me to start cumming. I cried out as he continue to fuck me, my cum covering his cock.

"Fuck," I heard him say as he pulled out of me, his cum splattering my stomach and chest. I ran a finger through it and put it in my mouth, wanting to taste him. He stared down at me, watching me taste him. "God, Laura." And then he leaned down to kiss me.

--

The next morning, I was sleeping on my side when James moved in close behind me. As I started waking up, I felt his hand running over my naked body, starting on my waist, then sliding over my stomach and up to my breasts. He clearly wanted more of what he had the night before. "Mmmm. Good morning."

"Good morning, Laura." He played with my breasts, softly squeezing and running his fingers over my nipples. Then his hand moved back down my body. His fingers found my pussy and started rubbing. I felt his cock press against my ass as his fingers probed into me.

It wasn't long before his cock replaced his fingers, gliding into me, our bodies starting to rock. He grabbed my tit as I pressed my hips back, feeling him move deep in me. His hand slid back down my body and started rubbing my clit while he fucked me.

"Mmmm, oh, yes." The sensations took me over, and I started to cum. I felt James thrust into me one more time and hold himself there as he came, too. We laid together, breathing heavily, his cock still in me as I turned my head and kissed him. What a way to wake up.

Before we went our separate ways that morning, James kissed me outside of the hotel and then said, "My assistant will be calling you today."

Later that day, I received a call, and by the end of the day, all my bills were being forwarded and a credit card was delivered to my door.

--

It's hard to believe that was just a few weeks ago. As the plane landed in Miami, James said, "I have the evening planned for us. And I picked out something for you to wear--it should be waiting at the hotel."

I smiled, "Sounds good." I couldn't wait to see what this trip had in store for us.