My first time having sex was when I went on vacation in Hawaii to take a break from my career as a singer, that was currently blowing up. I had just turned 18 years old a few months ago when I was on the plane out over the ocean. The only thing that I could think about was landing and heading directly to the beach. My friend came along with me, so I would not be alone on my first adult vacation. On the plane I was wearing in a large shirt that hung loosely over my body. Matched with an oversized pair of jeans, so that I was able to cover my body from the cameramen waiting for me at the airport exit. They knew I would be landing there sometime today and were determined to snap some photos before I got away to a private resort. Underneath the baggy close I was already wearing my black two-piece bikini that I was ready to feel free in at the beach. I walked past the paparazzi and got into my ride waiting with my friend as the lights flashed from the photos being taken. Once I was in the car, I knew that I was free from the media for the next week. We rode to the resort where we was met by a woman who greeted us. She was the owner and quickly introduced us to the man who would be serving us this week. A man came with a golf cart to pick up our bags and take us to the house we would be staying in a house over the water off the coast. He was barely older than me, maybe being 22. While driving to the home we would be staying at for the week, the driver told us his name was Kane. He was a fit boy wearing a white polo and khaki shorts that seemed to be his uniform for the resort. Kane was a Hawaiian born man from a father from the island and a white mother from Texas. We made small talk on the ride over, also learning that he was the room service man for the resort for the past two years. Promising to bring us anything we needed to make sure the vacation was perfect. We drove across a wooden dock that had houses on stilts over the water. Our place was the last on on the dock, giving us extra room in the water on one side. Kane put our bags in the two bedrooms inside, before reminding us to call for anything and leaving us alone. Rosie started unpacking, but I was just ready to be free in the water.
I took off my extra-large shirt and threw it down on my bed before I did the same with the baggy pants. While I was just about to leave the house I switched from white sneakers to a pair of black flip flops. While walking out of the room I caught a glimpse of myself in the mirror wearing my bikini. I had to stop and check out my nice body. It was hidden so much from the public that I forgot how I looked sometimes. My black hair was up in a ponytail over my head while I was wearing no makeup on my young baby face. At 18 my body was just perfect since it had just became fully developed. The black bikini was fitted nicely, propping up my already perky 34D breasts in the tight top. Looking down I seen my wide hips and thick thighs uncovered in the bikini bottoms around my waist. Two strings held it up on my hips while the cloth covered minimal skin. For once I was going to be able to not be fully covered when I am outside. My skin needed the sun since I looked like a pale goth girl with black and green hair. After I was done hyping my confidence up in the mirror, I went out to the back deck of the house. There was a ladder and a slide down into the water. I climbed down into the water and just floated on my back. Feeling like an animal who was just let out of their cage finally. The sun felt warm on my wet skin in the crystal clear water. While floating I heard a voice yell up from the deck, startling me as I was dozing off in the ocean.
Looking up I saw that it was Kane, asking if I was settled in and needed anything. I swam over to the ladder after thinking about some things we would be wanting today. Kane helped me as I climbed up the ladder, telling me to be careful not to slip. His strong hands held my hand and forearm when I stood up from the last step. I thanked him for the help. Then told him about the meal we was planning to have for dinner. Also Rosie had needed some special foods since she had allergies that I warned him about. He was so nice while taking notes to be sure not to mess it up. Kane’s tanned brown skin was almost a dark golden color in the bright sunlight. After he finished writing down our few requests, he joked about us being less demanding and needy than most the celebrities that came through the private resort. The compliment made me blush a little before he left to get everything we needed. Sitting out in the sun on a lounge chair on the deck I dried out my bikini. Once I was back to being dry I went inside to see if Rosie was done settling in. She was just getting out of the shower when I came in. Wearing only a towel around her body with her blonde hair down and sticking to her shoulders. While telling her about sending Kane after our items, I joked about her body being so thin. Our bodies were opposites completely. Rosie was a skinny tan blonde girl who was 5 foot 8 inches, while I was a thick dark haired pale girl who was only 5’3. We always made fun of each other for being too tiny or curvy. Her small boobs were barely able to hold up the white towel as she went into her room.
After taking a shower I took a short nap in my room. It felt amazing not to be worried about everything in my career and personal life on my get away. Falling into a deep sleep for two hours before a knock on the door woke me up. Climbing out of bed to answer the door my hair was a mess in a bun over my head. My light blue eyes were half open as I answered the door. When I seen it was Kane my body perked up and my eyes were fully open without thinking about it. He dropped off the food for dinner, with the few other items we needed. Before leaving the Hawaiian boy told me that he was going on a small boat ride around the coast if we would like to come. Rosie said that she was going to lay out on the deck and take in the night sky, but I told him that I would love to go out tonight. Kane said he would be back around eight, which was in two hours. Once he left I sat down with Rosie having dinner. She was a picky eater so it was nice her food was done right. We talked about going out tomorrow for a tour that we booked and then going to a restaurant on a boat for dinner. The day we had planned was going to be amazing. After dinner she went out onto the deck in her tiny white bikini while I went to get ready for tonight in my room. First I decided to wear a black tank top that was going to be over my white bikini top that I switched into. Making sure I was ready to swim if that was part of the plan. I was hoping to get into the ocean tonight with the moonlight. Over my matching white bikini bottoms that did not have strings, I was wearing a bright green sheer dress wrap. While I was putting my hair up in a bun I heard a little honking noise from out of my window. When I looked out the glass I saw Kane on a small boat waving up. Smiling I waved back and then ran over to slip on my black flip flops. When I came out to our back deck he was talking to Rosie since he pulled up to the ladder. He helped me down into the boat before we said goodbye my friend and drove off into the night over the water.
There was something about Kane that made me feel safe enough to ride on a boat with a storage man I just met on an island in Hawaii. I thought that it might be my mind letting me just be free for a while finally. He pointed out landmarks and fish as we drove around the coast. The only light was gleaming from the moon and the one lamp on our boat. The light reflected off of the water allowing us to see nearby fish. Kane was funny as he joked about life on the island being different than in a city like I was use to. My envy for his freedom began to grow as he told me that this was a normal night for him here. We started talking about our majorly different lives, comparing the things we some how had in common with each other. A island man who has never been outside of Hawaii except on boats in the water. A famous girl who travel the world performing for millions of people before I even turned 18 recently. There was no way we could be any different, yet somehow he made his life sound like mine. Kane was making the things I take for granted sound so much more important. We were halfway around the island before I noticed his joyful brown eyes in the low light. Our eyes locked after I told him how great life here sounded. His eyes were dark and dreamy while he stared back into my light blue and almost grey eyes. Kane was so sweet when he asked if he could kiss me. I knew that I should not be kissing a strange man, but something about him made it impossible to resist. He was the freedom that I was desperate for as I nodded my head up and down.
When Kane leaned into kiss me I felt his warm lips press against my plump pink lips. Our soft wet mouths began pull apart as we opened our eyes to see each other. I could feel my face becoming flush as I could not stop my lips from turning to a smile. Then I placed my hand on the back of his neck, pulling him in for another kiss. This time it was deeper and more passionate than before. Our lips pulled at each other as they separated. My hand was rubbing on the back of his neck on the edge of his hair. His hand moved up to my neck. The soft hands sent a pleasurable tingle through my body as they brushed into place against the skin of my neck. A little moan left my mouth when my neck curled to his touch. Something about this man was perfect and made me loose self control. My tongue teased his lips now as we kissed on the boat drifting slowly away from the coast. Then when I felt his tongue come back and touch the tip of mine, I was fully into it. Letting my tongue slide into his mouth and glide across his. Flicking it around inside of his mouth before pulling away. Teasing with my teeth while tugging at his lower lip playfully. Then I smiled at him as I wrapped my hands around his neck. My body climbing over the boy as I sat down in his lap in the boat seat. My thick thighs resting on his as I hug him closely. We begin to make out again with me in his lap. I can feel by big boobs squishing against his firm chest. With my legs spread over his lap the dress material I was wearing had came untied and now laid on his knees. Now I was only in my white bikini with the tight black tank top over it. His big hands began to run over my back, making me moan slightly as they ran up my spine to my neck. I pulled back from our kiss, looking into his dreamy eyes for a long moment. Right when I seen him open his mouth to question me, I flicked my tongue across his lips. The man froze as I winked at him with my blue eyes. When I felt his erection press against my thigh through his shorts, I knew that he was enjoying himself too. My virgin vagina was wet, I could feel it in the dry bikini as we kissed. I did not know if I was going to actually let him be my first, but I always got turned on from kissing. The furthest I ever let any get was the time me and my friend ate each other out. One time I had also jerked a boyfriend off, but did not finish it since we was almost caught. Tonight I did not know how far I would let it go, but I was ready for more teasing anyway.
When I teased Kane about his boner, he got a little red in the dark cheeks. Saying that it was not his fault that I climbed onto his lap. I agreed before giving him another kiss. Then I asked him if he did this with every girl that comes to stay here. He said that he did not, but I did not really believe that. Even knowing that this was probably his move with tourists, I did not want it to end there. My soft lips started to kiss on his neck, While I was teasing him, I felt his hands slide down my back to my wide hips. They rested there for a moment before he went down to my thick thighs. His strong hands squeezed my squishy pale thighs slightly, before sliding up under the tank top. For a moment I thought about stopping him, but quickly decided to let them roam. Then leaned back from his chest. My boobs readjusted in the top below as they were dropped from his body. I crossed my arms over my head and took off the black tank top. His hands were on my ribs when I dropped it to the boat floor. Kane finally got to just stare at my big breasts in the top like he wanted to when he first seen them in the water earlier. I had never met a man that seen my chest and not wanted to stare for at least a moment. It was a blessing and a curse. When I saw him break a smile while staring at them with his dark eyes, I giggled at the boy. That broke his stare from my chest. When he looked up, I joked about giving him a closer look before pressing my breasts into his face. Kane’s mouth and nose was deep in my cleavage when I felt his warm breath against my skin. That sent another tingle through my body. My nipples were poking through the bikini top cloth when I pulled back from his warm face. There were two tiny bumps in the bikini when I looked down at the white top. I put my hands over them to hide the excitement. He grabbed my wrist, pulling them away slowly. Then he said in a sexy accent that I got to feel his already. His hands went to my chest again. Mine rested on my thighs while he squeezed my huge breasts in his strong hands. Kane smiled when he felt how heavy the large mounds were. If he was gonna feel me up, then I was gonna do the same. Biting my light pink lip as I reached down between my legs. Below I found his erection in the cargo shorts. My fingers slid across the thick shaft under the cloth. I could feel it stiffen up as he felt me touching it.
When I began to touch his hard dick, Kane took that as an invite to pull my bikini top to the sides. Exposing my big D cup pale breasts that now had red tan lines from the bikini today. My nipples were hard in the center of the big pink areolas. Normally I was self conscious of my big nipples, but with Kane on the boat I felt free. When his mouth moved to breasts I felt myself perk up again. His lips were gentle on my nipple as he sucked at it. I let out a sexy moan that made him look up at me. My hand now squeezed on his dick in the shorts. It throbbed as I pressed it hard against my palm and his thigh. Something about this night made me want to try giving a blow job for the first time. I had done it on a dildo before with friends at a slumber party and even by myself a few times at home. It was time to see if the skills would translate to a real dick. One of my hands moved up to Kane’s forehead over my breast. Then it pushed his head away from the nipple he was sucking on. He looked up confused, before I crawled back down from his lap. Until I was on my knees on the floor of the boat. Sitting between his legs as I slide my hands up his hairy thighs. Slipping under the bottom of his boxers so I could find the hard cock. Looking into his dark eyes with my seductive blue eyes. When my hand gripped around the head of his dick on his thigh, Kane’s legs spread wider open around me. My soft fingers glided all around the crown as he began shifting in his seat. In the most sexy voice I could do I told him to take off his pants for me. He asked if I was sure shyly. I began to think he did not do this with every girl or was good at playing the role. I did not care much either way. Placing my hands on my hips and tilting my head, I gave him the signal that I was serious as I teased him about being shy. His face was red when he stood up and unbuttoned the shorts. For some reason I felt eager to put the dick in my mouth. Maybe this was part of being an adult felt like I thought. After unzipping his shorts, I reached up around the waistband and pulled down on them. The khaki shorts fell to the floor leaving him in only a pair of grey boxers. His boner was making a tent in the front of his underwear, giving me a good idea of how big it really was. Then my hands went to the top of the boxers and pulled them down too. His cock was dark and at least eight inches long. When my hand wrapped around the center of the shaft I realized how big it really was. My tiny hand could not wrap around the entire base. The finger nails just almost made it long enough to touch the thumb to my other fingers. Now I knew that his dick was much bigger than the little toys I practiced on. I was nervous as he sat back down into the seat with his hard dick facing back at me. Kane asked if I was sure I wanted to do it when he noticed I was hesitating. Finally I told him it was my first time doing any of this. He said I did not have to, but I told him I wanted to. He promised to be gentle and not go too fast as he kissed me on the forehead. Kane was the sweetest guy I had met, I felt so happy that I was going to let him be the first man in my mouth.
Slowly my head moved down to his erect dick in front of me. The size difference from my toys worried me, but I was determined to do my best for my first time. His brown eyes followed my mouth as it wrapped around the dark crown. I looked up at him for a sign that it was good while teasing the tip like I practiced on my toys. Slurping on it as I let my tongue stroke against the head. Kane put his hand around the bun on my head, pushing gently down so I would take in more than the head. As it slid into my mouth I felt it sliding across my tongue down the shaft. Half way down it was hard to breath as the girth filled my mouth. My head pushed back against his hand when it caused me to gag. Kane let my head up so I could catch my breath. He said he would stop, but I cut him off my taking the cock back in my now slobbery mouth. My eyes began to water from gagging on the head when it hit my throat last time. Again he was working himself deep into my mouth. This time I got a little more than half in before I had to pull back. I was surprised by how horny I became sucking a dick. Testing myself and pushing the limits had me hot. Then I went back down, Kane removed his hand and sat back in the seat. He guided the boat back in towards land slightly, since we had drifted pretty far out. The whole time I was on my knees working up and down on the dick. Taking in half his length while bobbing my head down on his boner. A few time I gagged when I pushed deeper than I could take, but I felt like I was getting the hang of it. Then I got a good sign that I was performing well. In my mouth I began to taste a saltiness in my throat that I had head would happen when they got closer to finishing. My friends had said the precum meant that they were trying not to bust yet. That made me feel like I was working for something now. I tasted the precum and my mouth worked harder to milk the load from his cock. My hand moved to the base of the shaft so I could move my mouth faster. There was saliva dripping from my chin now. As I was stroking him inside of my mouth, I remembered that men loved having their balls played with. My ex boyfriend use to make me play with his all the time when we were hanging out. I never did more with him than that. Once I remembered that I ran my free hand up his hairy inner thigh. Following the leg up to his scrotum. When my hand gently grabbed the slobbery sack, Kane’s hip tensed up and I could see his thighs flexing. My mouth smiled on the dick while looking up into his dark eyes. He was not looking down at me, but out into the water. I thought he was trying not to cum. My fingers juggled his balls in my palm while my mouth continued working the shaft. Finally he grunted out that he was going to cum. I pulled my mouth from the dick, opening like I see the girls in porn do. I figured that was what he would want me to do. Kane stroked hard at his cock with hips hips bucked up from the seat. His hand went across the wet skin rapidly until he finally reached his climax. The cum sprayed across my face, covering one of my eyes that was now closed. I watched the load continue to squirt out onto my forehead and mouth. When it hit my tongue the taste was overwhelming for a moment. Before my mouth fully closed I stopped myself and held it open like a good girl. The cum began to drip out in spurts from the dark tip. Warm drops of cum fell down on my exposed breasts. That feeling of warm sperm on my tits was close to the feeling of a warm hug as a praise for a good job. Kane sat up in his seat upright again, looking down at my cum covered face. He said that I could use his shirt to clean myself up, but I denied. Either because I did not want to ruin his shirt or because I wanted to wear the cum proudly. Then we got our clothes back on silently. After my first blowjob we drove the boat back to my home, where I invited him in for the night.
When we climbed up the ladder we went into the back doors, walking through the kitchen towards my bedroom. Rosie was on the couch watching tv and looked back asking how the boat ride was. I told her it was fun and quickly looked away and straight towards my door. Kane followed behind me. Once inside my room I surprised that she was still up this late and scared that she may have seen the drying cum on my face and chest.. My nerves were calmed when the man grabbed me from behind. Squeezing my thick ass and calling me a freak for walking around with his sperm on my face. The Hawaiian boy could get me to do anything with those eyes and that accent. He laid me back onto the bed. Kissing me on the stomach. He kissed down the center of my chubby stomach to my bikini bottoms. I could feel how wet I was and the warmth between my legs as his lips pressed against my virgin vagina over the bikini. His fingers grabbed onto my bottoms, pausing while asking if I wanted him to eat my pussy. I bit my lip and agreed once again. Kane pulled the panties down slowly. His warm lips kissed against my inner thigh. My entire body got chills as he worked his way back to my bare vagina. I did not plan on sex, but lucky I had trimmed my pubes up into a neat triangle for the bikini last night. Instinctively my hand went into his brown hair and my thighs squeezed gently around his head when the tongue touched my wet lips. Looking down I could only see his head moving around from above while he was opening my labia up with his wide tongue. His mouth felt so much different than the times a girl had done it. It was a bigger tongue, but also it moved more determined and less precise. Although it was different, the wet tongue felt amazing as it slid into my virgin hole. He pushed it in as deep as he could go. Swirling around in my vagina. Clearly he had done this before at least. Then it exited, taking my breath away in a gasp. His tongue felt wetter as it slid up to the top of my vagina. Kane flicked his tongue across my clit. That was my favor part of masturbating, teasing my sensitive little pink bean. His lips locked on with suction and I could feel it circling the pink clit. His mouth was rubbing against my clit in between the teasing flicks of the tongue. Since I rarely had sexual encounters in the past it did not take long for the dark skinned man to bring me to an orgasm. This one felt much different than with a gentle girl though. As my legs tried to lock around his head, Kane pushed them wider open and held me to the bed. That dark hair bouncing around over my vagina as his tongue worked hard to please me further. My legs shook uncontrollably as I moaned in quick gasps. Kane pushed me harder and harder until I had to shove his head away from my vagina. My face was bright red after the intense climax. He was not going to stop until I forced him to. I could tell by the happiness on his face. Kane stood up with his face wetly covered by my pussy juices. Never had anyone made me cum so hard that I needed to take a minute to catch my breath after. When he was standing over me beside the bed, I could see he was fully erect from making me orgasm in his mouth.
My finger motioned for Kane to come closer to me while I bit down on my lower lip. When he got just close enough I hooked my hand around the back of his neck. Pulling him down onto of me quickly giggling and kissing his wet lips. The kiss allowed me to taste how my vagina was tonight for him. It was something I always did when my friends would lick my pussy during sleepovers or when I rubbed myself home alone. Tonight it was good and I felt it was sweeter from his lips for some reason. Maybe I was just overly aroused by the exotic man in my bed tonight. Then I kissed up his cheek to his ear lobe. Our cum mixed as I touched his wet face to my sperm covered pale face. When I got to his ear I whispered softly that I wanted him to take my virginity from me. His dark eyes looked up at me when he lifted his head away. The surprise that I was wanting to let him be the first man inside of me was a pleasure to see. Kane asked if I was sure, trying to be as nice as possible. Probably trying to also hide his excitement from me, at least I liked to think. I said in a seductive voice that I wanted him to fuck me tonight. He slowly stood up at the edge of the bed between my legs after I confirmed my sexual desire. That dark fat cock rest on the pubic mound above my vagina. He asked if I wanted him to put on a condom. That had not crossed my mind before that moment. Stopping to think for a second. I decided if I was being this free on my vacation then I needed to feel it all inside me uncovered. Playfully I asked if he was clean and told him we did not need it. Telling him to be sure to pull out before cumming. Then he took the head of his cock and rubbed it against my wet vagina. Lubing it up with my own bodily fluids before trying to push it inside of me. The girth was hard to squeeze into my virgin pussy. Slowly he was able to work the thick crown into my body, causing me to moan with each bit of progress made. After the rim of the head, he was able to get in a little more before I felt the tip painfully pressing against the hymen. I assumed that had broken in the past. Although I had dildos, I only practiced sucking them or stroking them for when I was with a boy. Rarely I would get fingers in there but never dared to go deep. Normally I stuck to just rubbing the outside or the clit. That was typically enough, but now that the thick shaft was trying to break me open my body was wincing. Kane stopped asking kindly if he should stop. I just wanted it to rip so we could get on with it. My body was craving him. Then I took my legs and pulled him in by the ass. The tip tore through my hymen making me scream out for a short moment before remembering that Rosie was here too. By the time he pulled his cock out the pain was almost gone. It was a pleasurable pain now. The dark dick had my blood on it, as he pushed the fat cock back inside my pussy. Again slowly spreading me open as he got deeper inside that before. Kane kept traveling up inside of my body until his hips hit against my body. I felt full of the fat cock when he got deep into my guts with it. Then he was pulling it back out of my deflowered hole.
After a few slow strokes deep inside of me to get me adjusted to sex for the first time. I felt his pace start picking up. His hips now pressed harder against me with each pump forward. The harder he went into my body, the more turned on by his powerful thrusts I was. Kane held my legs open by the thigh right above my thick ass. My finger went to my mouth as I bit down on the tip. The other hand played with my boobs that were being pulled out of the white top. My boobs were squeezing out of the bottom. The pale mounds showed blue veins lightly under the skin and my nipples were slight brighter pink than normal. Once they were out I saw Kane watching them jiggle with each pump inside. That fat dick was so good that it made me moan when it was fully in. The horny Hawaiian man was humping me harder to make my tits bounce on my chest. He clearly was obsessed with my boobs like all the other men I have met. I told him to help take the top off. He bent down over me, with the dick deep into my vagina and pulled the top over my head. Once I adjusted my pony tail, I decided to let my hair down. The hair type fell onto the bed as I rolled it down my dark hair to the green tips. Then I was laying back on the bed normally when my first man started to fuck me again. Now he held me tighter, thrusting into my thighs with more force. Our legs clapped together as the skin collided. He had my free breasts bouncing across my entire chest. Seeing him so determined to fuck me harder was a major turn on. Soon the feeling of the man inside of my pussy for the first time was more than enough. The cock was throbbing deep inside of me. My legs tighten up once again, this time shaking in the grip of his hand. It felt like my vagina was pulsating with him deep inside. I was orgasming to my climax quickly while biting down on the sheets. Then the dick was yanked from my pussy as he grunted out above me. Kane held his eyes tightly shut and stroked at his dick for a second before it erupted with cum. The white load blasted across my stomach and all over my dark blonde pubes. Ropes launched across my lower body as my climax drifted away to an end. My fingers ran across some of the sperm, collecting it on my finger. I brought it to my mouth to taste it again. Something about sperm made me always need to taste what we worked hard for.. Just needing a little taste each time. After the orgasm he stood letting his dick drip out the last bits of sperm while my legs relaxed off the edge of the bed around him. Kane asked how it was for me before laying down naked beside me. I leaned over and kissed him on the cheek. Telling him that it was the best I ever had as a joke. Then honestly letting him know that I enjoyed my first time having sex with him and that I made the right choice. We cuddled up in the middle of the bed and I fell asleep in his arm and covered in his dried cum.
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Source: reddit.com/r/eroticliterature/comments/hy9dag/billie_loses_her_virginity_on_an_island_vacation
So Sexy!