Trip with My Sugar Daddy Ch. 02

When James and I arrived at our hotel in Miami, we took the elevator to the top floor. When the elevator opened, I could see across the suite to a set of french doors leading to a balcony overlooking the ocean. The view was amazing. James saw the look of awe on my face and smiled, "Nice, right?"

"It's beautiful." I walked out onto the balcony to take in the view.

James came out and put his arm around my waist. He leaned in and kissed my neck. "Why don't you get ready? Dinner is in an hour. I have a couple calls to make." I knew that meant he was probably calling his wife, but I tried not to think about it.

James left the suite, and I hopped in the shower. I started thinking about what he had done to me on the plane--his fingers inside me, my breast almost completely exposed as he groped me. It was enough to make me start touching myself. I slid a hand over my breast, softly rubbing the nipple. Then I moved lower, stroking my pussy, feeling my own wetness start to mix with the water from the shower. I had to force myself to stop. I knew there would be plenty more to come during this trip, and I didn't want to get too carried away yet.

When I was done showering, I pulled on a robe and walked into the bedroom. There was a very sexy white sundress laid out on the bed. Apparently this was my outfit for the evening.

The dress was low cut, with off-the-shoulder sleeves. I picked it up and turned it around. The back was cut even lower than the front. No way to wear a bra with this. I was nervous about wearing a white dress without a bra. I hoped it wouldn't be too sheer.

I put on a white thong then pulled on the dress. Looking in the mirror, I didn't think my nipples were too noticeable. Even so, the top barely came up over my breasts. One wrong move and anyone who happened to be looking would get a show. The skirt flowed and stopped a few inches above my knees. An ocean breeze would make this a very interesting dress to be wearing tonight. James knew exactly what he was doing when he picked this one out.

I did my hair and makeup and was finishing up when James came back. "Wow, Laura, you look amazing."

I grinned, "It's a great dress. Thank you."

He leaned in and kissed me. "Let me get ready."

It wasn't long before he came out of the bedroom, wearing tan linen pants and a white button-down shirt with the sleeves rolled up. God, this man was sexy. I walked over to him and put my arms around his neck. His hands came to my waist as he leaned down and kissed me. He pulled back and smiled at me, "If you keep pressing up against me in that dress, we're not going to make it to dinner."

I laughed and pressed against him harder before pulling back. "Let's go."

When we exited the hotel, there was a small sports car waiting out front. "This is us," James said. "I'm going to drive tonight." He opened the passenger door for me, and I got in.

On our way to the restaurant, James was talking about the area of Miami we were in, pointing out different places. He reached over and put his hand on my leg as he talked, his fingers softly brushing up my thigh, causing the skirt of my dress to move higher up my leg. I was trying to listen to him, but my attention was on his fingers.

The restaurant was a short drive away, and his hand left my thigh disappointingly soon. "Here we are," he said as he pulled into the valet area.

The valet walked over to the passenger side and opened the door for me. I saw him glance down and quickly glance back up, his face a little red. I looked down and realized that one side of my dress was still pulled up almost entirely over my leg. I quickly pulled it down as I swung my legs to get out of the car, only to realize that doing so simultaneously lowered the top of my dress. The valet looked back down just in time to see some serious cleavage. This time, he didn't look away.

By this point, James had come around to my side of the car. I managed to pull my dress up and get out. He smiled and held out his arm for me. As I took it, he leaned in and said, "I think the valet enjoyed watching you get out of that car."

We were escorted to a table out the back of the restaurant. It was basically on the beach, and the view was great. James ordered us a bottle of wine and a delicious selection of seafood. The waiter brought our wine and poured us each a glass. We clinked glasses as James said, "Here's to what will be a very enjoyable trip together."

At one point while we were waiting for our food, I dropped my napkin. I reached down to pick it up and felt the top of my dress fall dangerously low again. I sat up and went to pull it back up, but before I could, James said, "Leave it."

I looked over at him, unsure if I heard him correctly. He smiled and repeated, "Leave it." I dropped my hands from the top of my dress and looked down to assess the situation. The dress was even lower than it had been with the valet. It was just barely over my nipples. In fact, from my point of view, I could see the tops of them, but unless someone was standing right over me and looking down, I thought I was still okay. I looked back up at James, who said, "You look amazing. No need to cover up."

Before I could respond, two waiters arrived with our food. One came around to my side of the table to put the plate in front of me. I started to panic a little when I realized he was standing right over me, at just the right angle to look down my dress. I just hoped he would be so focused on the food that he would ignore me. He leaned down and set the plate in front of me. As he stood back up, he looked down at me and started to ask, "Is there anything..." and then he paused mid-question, staring at my breasts. It only took a moment for him to gather himself, but there was no question as to what made him pause. He finally managed to ask, "Is there anything else I can get for you?" with a grin on his face and his eyes still glancing down my dress.

"Not for now, thanks," I responded. I had expected to feel embarrassed by this situation, but instead I found myself surprisingly turned on. He waited just a little longer than he probably should have, then turned and walked away with the other waiter. I saw them glance at one another with grins on their faces as they left the table.

I turned to James, who was also grinning. I laughed and asked, "Can I pull my dress up now?"

"One thing first." James leaned over the table and brought his hand to the side of my face, pulling me toward him. As I leaned across my side of the table, I felt my top lower even more, one side falling below my nipple. James looked down and smiled, then he pulled my face into his and kissed me. As we kissed, his hand moved from my cheek, down over my neck, then over the top of my breast. Then he started softly stroking my exposed nipple. At this point, I was so turned on that I don't think I would have stopped him if he had pulled the top of my dress down around my waist and taken me right on the table.

After a few more strokes, James pulled away from me. "Now you can pull it up. Let's eat."

I tried to catch my breath as I pulled up my dress. I glanced around at the other patrons, but I couldn't tell if anyone had seen us. It was too late to care now anyways. As I started to eat, I could only hope that there wouldn't be a wet spot on my dress when I stood up.

--

After dinner, the same valet retrieved our car and was extra friendly to me as he opened the door. As I got in the car, my dress billowed up, giving a quick flash of my thong. I looked up and smiled at him as he shut the door. James laughed. "I don't know why I bothered tipping the valet--you've given him quite enough."

As we pulled out, James started rubbing my leg again. "What a night. Let's take the long way back to our hotel."

"Sure," I answered, but I was a little disappointed--I wanted to get back so we could finally be alone. I needed some relief from this evening of teasing. Even now, James' hand was driving me crazy, sliding up my leg, pulling my dress up with it. The higher his hand moved, the more my pussy throbbed, wanting to be touched.

Finally, while we were stopped at a red light, James' fingers found my pussy, rubbing softly. I moaned quietly, my eyes closed. His fingers pressed harder. "Look at me." I looked over into his eyes as his fingers continued to move. My panties were soaked. "That's it. Get nice and wet for me."

The light turned green. He started driving again, but his hand kept moving. I felt an orgasm building when he pulled his hand away and moved to the top of my dress, pulling it down, completely exposing my breasts. It was dark out, but we were still in a city full of lights. "What if someone sees?"

He glanced over and grinned. "Let them see how sexy you are." His hand moved over my breasts, pulling on a nipple, then went back down between my legs. He started rubbing my clit. I leaned back, so turned on knowing how exposed I was. His fingers moved over my clit, then thrust up into me, then went back over my clit. We came to another red light right as I started to cum. James pressed his fingers into me, feeling my juices come out of me. "You look so good when you cum, baby. I think the guy beside us agrees, too."

I opened my eyes and looked over in James' direction, noticing that there was a man driving a car in the left lane beside us. He was looking into our car, clearly seeing what was happening. When he saw that I noticed him, he looked away. But then he quickly looked back over, unable to take his eyes off my tits. This felt like the world's longest light.

James laughed, and I looked over at him and then down, seeing his hard-on in his pants. I smiled and said, "May as well give him even more of a show." I leaned over and started undoing James' pants. He looked surprised but definitely not upset. I heard him take a deep breath as I pulled out his cock, wrapped my fingers around it, and started to stroke.

At this point, the light turned green and James started driving again. He moved his right arm for me as I leaned over and wrapped my mouth around his cock. "Fuck," he moaned. I spent a few minutes just enjoying his cock, licking the tip, then sliding my tongue up and down, stroking it with my hand. Then I finally took it in deep, hearing James moan. I started moving it in and out of my mouth, continuing to lick and suck until we were a few minutes from the hotel.

I felt James' hand on my head as he said, "Okay baby, we're almost there." I didn't want to stop, but I knew we needed to make ourselves look half decent. I slid his cock out of my mouth and leaned up, pulling my dress back over my tits.

At the stop sign before our hotel, James put his cock back into his pants and zipped up. He looked over at me, his eyes full of lust. "I can't wait to get you in our room."

--

When we got back to the hotel, James quickly ushered me toward the elevator, where an older woman was already waiting. James nodded a hello to the other guest, but I could see his frustration that we wouldn't have the elevator to ourselves.

We stepped into the back of the elevator and the woman followed, standing in front of us, facing the doors. James put his arm around my waist as the doors closed, and I felt his hands start to move over my ass. It didn't take long for him to start to pull up the back of my dress until my ass was exposed, his hand massaging it and playing with my very wet thong.

We reached the woman's floor, and she turned her head and said, "Have a goodnight."

"Thank you, we will," James replied. I started laughing as the door closed behind her. James quickly pulled me into his arms and lifted up the entire skirt of my dress, his hand still exploring my ass and pussy. He whispered in my ear, "I think being exposed excites you" and kissed down my neck.

I breathed heavily as his fingers ran over my pussy. I could feel him getting hard again as he pressed against me, "I'm not the only one who's excited." I ran my fingers over his pants, outlining his cock.

Just then, the elevator doors opened into the penthouse. James led me into the room and stopped me as I was facing the open french doors, the ocean breeze coming through. He stood close behind me. I felt his breath on my neck as he whispered, "You look so sexy."

He started kissing my neck, slowly. Then brought his hand up around it, gently squeezing as he kissed. My breath caught in my throat, so turned on. Then his hand moved from my throat, down to my breast. He pushed the top of my dress down as his hand cupped my breast, now totally exposed.

I reached back and started rubbing his cock through his pants. I heard him moan as he pushed the other side of my dress down and pulled on my nipple, making me gasp. He moved us over to the couch and pushed me down onto it. He kneeled in front of me and took one of my tits into his mouth, softly biting. I put my hand on the back of his head and closed my eyes, each bite a fantastic mix of pleasure and pain.

Then he pulled back and lifted up the skirt of my dress. "I need to taste this thong." He moved his head between my legs, pulling them up onto his shoulders. I felt his lips on my thighs as his fingers rubbed my pussy, making me even wetter. His tongue soon replaced his fingers, and I felt him licking my thong. His tongue pushed the fabric over my clit. It felt amazing. He looked up at me and smiled, his fingers continuing to rub. "It tastes so good." I felt his fingers start to press up into me, thong and all. I moaned as his fingers probed me.

He put his head back down and started sucking on my clit through my thong. LIfting his head up, he said, "I think you should taste this." He leaned in and kissed me hard. I could taste myself on him as I kissed back. I felt him slide off my thong. He bent back down and started licking my bare pussy as he slid his fingers back into me.

I reached up and started rubbing my tit, feeling myself getting closer to the edge with each lick. He looked up at me, watching as I moaned in pleasure, pulling on my nipple. One more deep thrust of his fingers, and I lost it, cumming in his mouth.

James gave my pussy a few more licks as I laid back against the cushion, breathing heavy. Then he stood up, pulling me with him. "Don't get too relaxed, Laura." He stood me up. "This needs to come off." He quickly unzipped my dress and pulled it off of me. Then he pushed me over toward the bed. "Go lie down." I laid back on the bed, propped up on my elbows, watching him remove his own clothes. Without even realizing it, I had been stroking my pussy as I watched him. He smiled as he walked over to me. "I could watch you touching yourself all night."

Completely naked, he crawled onto the bed, getting onto his knees in front of me. He pulled my legs up and wrapped them around his waist. Then he leaned over and started kissing me as I felt his cock slide into me.

I moaned and bit his lip as he went in deep. He held himself in me as he kissed down to one of my tits, sucking on the nipple. I wanted to feel him in me forever.

James leaned up and started to slowly thrust. "I wanted to fuck you all evening."

His cock felt so good. I wanted more. I moaned out, "Go hard."

He smiled down at me and started going slower, teasing me. "You want me to go harder, Laura?"

"Yes, harder."

"Beg for it."

I looked up at him and said, "Please. Fuck me hard."

"That's it, baby." He put his hands on my hips and started thrusting into me harder, my whole body bouncing with each thrust. My hands were gripping the sheets, my pussy getting tighter around his cock. James continued to thrust into me with a power I've never experienced. It wasn't long before I felt myself cumming again, a loud moan coming out of my mouth.

He thrust into me one more time and held himself there as he groaned. I felt him cumming inside me. He leaned over and kissed me, his cock still inside me. "That was amazing."

Then he pulled out and laid down beside me. "Yes it was, baby." I was too tired to move. I felt his cum dripping out of me and onto the sheets as I fell asleep.