Eager First Times

by Betsy Locke

  She realized I was staring in one single direction. Her eyes followed my sight line and caught what I was looking at. “I think we found him.”

  I snapped out of it and laughed. “He's good looking but I'm not just going to go up and talk to him.”

  “Why not?” Piper asked.

  I couldn't find the right words. I didn't have a good enough reason other than I was too scared. “I don't know. It's weird to just walk right up to a stranger and start talking.”

  “You're doing this, Autumn. You're a hot older woman. This guy is going to be drooling all over you.”

  I lay back down and closed my eyes. A stirring between my legs was telling me to go fuck that guy right now in front of everyone. I could already imagining him pumping in and out of me, his long hair cascading over his tight body. I had such a filthy mind sometimes. I'm glad nobody could hear my thoughts.

  Piper could tell that I wasn't going to do anything about it. “Listen. You have two choices. One: You go up and introduce yourself to him. Or two: I go up to him, point you out, and tell him that you like him but are too afraid of passing your gonorrhea to him.”

  I jolted up and took off my sunglasses to look into Piper's eyes. “You wouldn't!”

  She shrugged. “It's up to you.”

  I groaned. I was almost ready to give up and just let Piper have her laugh. Why did I care if some random guy thought I had a STD? But that throbbing between my thighs was telling me to go for it. The worst that could happen is he turns me down.

  “You win, Piper.” I stood up and took in a deep breath. My heart was pounding hard in my chest. The tips of my fingers felt all prickly. I hadn't been this nervous in a very long time. I started walking towards the man, my feet sinking into the sand with every step.

  The gorgeous guy was still standing at the edge of the water, squeezing the water out of his hair. His surfboard stuck in the sand like it was Excalibur. What was I going to say to him? I turned around and saw Piper watching me intensely. That made me even more nervous to know that I had an audience to watch me crash and burn.

  His blue eyes spotted me coming towards him. He stood up straight and smiled. I lost all my senses and couldn't think of a thing to say. I opened my mouth to talk but nothing came out. This was already a disaster.

  “Can I help you with something?” he asked.

  I clenched my hands and steeled myself. “I'm Autumn,” I said, my voice a little louder that I would've liked.

  “Nice to meet you, I'm Grant,” he replied, taking my hand and shaking it. His handshake was so firm and I could feel the callouses on his palm.

  What was I supposed to do next? I was never very good at this type of stuff. I caught him checking out my cleavage and that gave me a burst of confidence. Maybe this guy was attracted to me. “I was wondering if you'd like to get a drink with me later at my hotel. The one behind me. Sometime after dinner?”

  It felt like I was waiting a lifetime for his response. “I'd love to,” he replied with all the charm in the world.

  Chapter Three

  “I still can't believe you did that!” Piper said as we walked back to the hotel room.

  “What do you mean! You made me.”

  “I know but I didn't think you would actually do it. So he's going to meet you at the bar outside after dinner?”

  I couldn't help but smile. “Yeah I think so.” A dreaded thought entered my mind. “What if he doesn't show up?”

  Piper stopped in her tracks and put both hands on my shoulders. “There's plenty of men on this island, Autumn. If this one doesn't work out. We'll find you another. We have two weeks in paradise. We won't let any asshole ruin it.”

  “You're right, Piper. He's just so dreamy.”

  “And younger,” she added.

  We returned to my room and I poured out the contents of my suitcase onto the bed. “What should I wear then?”

  Piper searched through my clothes and found a long flowing dress of blues and greens that had tropical flowers on it. “This one will be perfect. I remember you wore it a few years back and it definitely works for you. But let's try it on first.”

  I took the dress into the bathroom and changed. Piper was comfortable being naked in front of me but I wasn't. I slipped the dress on right over my bikini. It had been a while since I wore it last but it still fit.

  I came back out and did a spin for Piper. She clapped her hands. “It's even better than I remember it. Your tits are basically bursting out. He won't be able to keep eye contact with you for sure.”

  I never really liked to show so much of my breasts. I turned to the full-length mirror and tried to stuff them deeper down my dress but there was just too much. “Should I put my hair up or keep it down?” I did both to show Piper the two options. “I've never been on a date with a guy who had hair as long as mine.”

  “I think you should keep it down. Especially with that dress.”

  Piper and I got an early dinner downstairs at the hotel restaurant so I would have enough time to get ready. I wanted to look perfect for Grant. Piper offered to help me with my makeup but I declined. I needed some time alone to gather my thoughts and prepare for the date.

  Grant was meeting me at the bar next to the hotel pool. It was a small hut with seats all around it. I had gotten there a little bit early to make sure that I wasn't late. I didn't want to risk him getting there and leaving because I wasn't there yet. We never exchanged phone numbers so this was my one chance.

  The sun was setting as I took a seat at the bar. A bartender that was about my age with a bushy mustache walked over. “Can I get you something?”

  I was about to decline so I could wait for Grant but then I thought that I should loosen up a little before he showed up. If he showed up. “I'll get a mai tai.”

  It was hard to be nervous in such a relaxing environment but I was. The bartender brought me my drink and I took a sip. The burning alcohol danced its way down my throat. It was way too strong than what I normally liked but I needed it.

  A fire dance show was going off at another part of the hotel. I could hear the crowd and see the shadows dancing on the side of the building but I couldn't actually see the performance.

  “Am I late?” a voice said behind me.

  My heart jumped in my throat. The drink jostled in my hand as I spun around and saw Grant standing there. He was no longer wearing his wet suit but a nice button-up shirt and shorts. Still definitely Hawaii but a lot more dressed up than earlier. His long hair was gathered behind his shoulders. He didn't smell like the sea anymore but whatever cologne he put on was captivating. I wanted to jump into a pool of it.

  “No you're right on time. I was a little early so I could get a drink.” I lifted my glass up to show him that I already started.

  “You look beautiful,” he said, his eyes wandering over my dress. It was a simple yet effective compliment.

  I flushed and avoided eye contact with him.

  Grant took the empty seat next to me and signaled the bartender with a finger. “Can I get a whiskey and coke?”

  “Not into fancy drinks?” I asked, sipping the mai tai through the tiny straw. The alcohol was already going straight to my head. I hadn't felt this buzzed in a long time and I was barely through my first drink.

  “When you've lived here all your life, you can get a little sick of the island drinks. I still drink them from time to time.”

  I liked to watch the way his lips curled when he spoke. It was so cute. “So you were born here then?”

  Grant nodded. “What brings you to Hawaii?”

  I looked down at my appearance. I thought my dress was close to what islanders wore here. “Is it that obvious that I don't live here?”

  Grant brushed his finger across my collarbone. It sent shivers right down my spine. “It's your soft skin. It looks like it's never been touched by the sun.”

  I didn't care about the sun touching me but I wanted Grant to touch me more.

  Chapter Four

&nb
sp; “My friend kind of dragged me along with her,” I told him.

  “Was she the one that was staring at us when I first met you.”

  I laughed. “Yep. That would be Piper.”

  An awkward silence passed as we both sipped our drinks. Mine was almost empty and Grant picked up on it immediately. He snapped the bartender over. “Can you get the lady another and put it on my tab.”

  “You don't need to buy me a drink, Grant.”

  “Don't worry about it,” he said with a smile that could kill.

  For some reason I felt comfortable around him. He had to be in his late twenties but he felt even more mature than that. Maybe more mature than me. “What do you do for a living? I bet you teach surfing lessons.”

  Grant spit out his drink to the side. “Is it that obvious?”

  “Well to be honest, that's the only job I could think of for an island. It is kind of a cliché though isn't it?”

  “I guess it is a little. Have you ever surfed?” he asked.

  I took a drag of my drink and set it down, shaking my head. “Never in my life.”

  “Then I'm going to teach you.” Grant stated it like a fact. Like I didn't really have a choice in the matter.

  “You think I can actually do it?”

  “Anyone can do it. All you need to be able to do is lift yourself up off the board. After that it's cake.”

  “Well I've always wanted to learn.”

  “Then it's settled. Tomorrow morning, I'm going to teach you how to surf.”

  “Do you want to go up to my room?” I blurted out. I didn't even mean to ask him that question so soon. We were only on our second drink and only been talking for an hour. He probably thought I was the biggest slut.

  “That would be nice,” he replied.

  I was shocked. Completely floored. I didn't think it would be that easy. By the way he looked at me, I knew that he was attracted to me on some level. But I didn't think he would be that into an older woman. I guess I was wrong.

  We didn't speak much as we walked the lush green landscape of the hotel and to the elevator. His shoulder brushed against me every once and awhile and it sent my adrenaline rushing through my veins.

  We came to my room and I unlocked the door. I couldn't believe this was happening so fast. My pulse was thudding in my ears. I could barely hear myself think. I turned on a few lights and opened up the screen door so we could hear the ocean.

  “What's this?” Grant asked, holding a bottle of wine.

  That hadn't been there when I left. I notice a slip of paper attached to the bottle. I unfolded and read it aloud:

  Have a nice night.

  -P

  “You have a nice friend,” Grant said, walking around until he found a wine opener next to the coffee machine.

  “How the hell did she know we were going to come back here?”

  “She must know you better than you thought.” Grant pulled the cork out and poured two glasses of red wine. He handed me one and we clinked glasses.

  I definitely didn't need to be more drunk but it couldn't hurt. The throbbing need in the pit of my stomach was screaming at me to speed things up. I grabbed Grant's drink out of his hand and set it on the table. I needed to set the tone.

  I looked him deep in the eyes and told him exactly what I wanted. I stepped forward until we were inches away from each other. Our noses were almost touching. I closed my eyes and parted my lips. Grant slipped his hands around my back as our lips met.

  Excitement surged through me. Firecrackers were going off all over my skin. Grant pushed his tongue into my mouth and I could feel my bikini bottoms become wet. I broke away from the kiss and started to unbutton his shirt.

  I couldn't wait for him to take his shirt off before I felt his hard chest. My fingers ran over his taut muscles and down his to his washboard abs. My heart was beating so fast. It had been so long since I touched a man.

  Grant kissed me again, his hands feeling up my breasts over my dress. His mouth moved down to the soft flesh of my neck and he sucked on me hard. I moaned softly, my hand wandering down until I found his hard length in his shorts.

  “You're so big,” I exclaimed.

  Grant smiled before raining kisses across my collarbone. He pressed my tits together making a canyon of cleavage. He ran his tongue across my breasts, kissing me lightly. I wanted to feel his lips around me. I pulled my large boobs out of my dress and bikini top until they were all exposed for Grant.

  Tonight was far from over.

  Chapter Five

  “You're big too,” he said. Grant squeezed my melons with his strong hands until they were about to pop. He wrapped his lips around my pink nipple and sucked on each one until I cried out from the pleasure and pain.

  I couldn't handle it anymore. My fingers fumbled at the button to his shorts until they were finally undone. They fell to the ground and I realized that Grant wasn't wearing underwear. His large throbbing cock stood straight up, pulsing up and down.

  I went to my knees immediately. I gripped his base with both hands, wrapping my fingers around his impossibly wide girth. Grant ran his fingers through my hair and I looked up at him. Desire flamed in his eyes.

  My lips touched his head and brought a string of pre-cum along with it when I pulled back. I stroked him a couple times, my hands going all along his shaft. I opened wide and shoved his entire cock down my throat.

  Grant groaned loudly, holding the back of my head as he helped thrust in and out of my mouth. Even though I hadn't been with a man in ages, I'd had a lot experience with this before. More than probably anyone Grant had been with.

  “Fuck. That feels so good,” he yelled.

  I could feel his penis harden in my mouth and his balls draw up. He was close to coming. I wanted to feel his seed down my throat but I didn't want the night to be over yet. There was so much more that we needed to do. So much more that Grant needed to do to me.

  I pulled him out of my mouth and wiped the pre-cum and drool from my lips. Grant looked dazed for a moment as he tried to sift through the cloud of pleasure. “That was too good,” he said.

  I stood up. “I need you to fuck me now, Grant.” I pulled my bikini bottoms down and tossed them across the room. I didn't even bother taking my dress off yet. I walked over to the small couch and draped my body over the side. I pulled my long dress up until my ass was revealed.

  Grant approached me from behind. His hand lifted my dress further until more of my back was exposed. He grabbed my ass and spanked me a couple of times. I cried out from the sudden pain and wanted more.

  He gripped my curvy hips and placed his thick cock in between my ass checks. I could feel his warm shaft just waiting to unload all over me.

  His blunt head teased my wet opening, circling around and driving me crazy. I was just about to order him to fuck me when he drilled into me. An enormous amount of pleasure washed over me as my pussy took every inch of him.

  I never knew I could take somebody so big before.

  “You're so tight, Autumn!”

  Grant thrust forward until he hit the end. I wanted him to stay inside me like this forever. “Fuck me hard, Grant,” I cried out.