Every year, my family takes a summer trip when all of my siblings and I are out of school. It has been a family tradition for as long as I can remember. Usually, we would choose somewhere warm and sunny like Florida or Hilton Head, South Carolina, but on special occasions like major birthdays, graduations or things like that, my parents would splurge and choose somewhere more exotic like Hawaii, Aruba, Jamaica. I had just graduated from grad school, so this was one of those trips. My parents booked a family-friendly resort on the Island of St. John in the US Virgin Islands. This would be a great last hurrah for me before starting my first big-girl job, and I was very excited to celebrate becoming a real adult.
—–
The first morning we were there, my older sister Claire went down to the pool early to save us some chairs with a good view and close access to the bar (since Daddy was paying for the trip, we didn’t plan to be shy with the fruity rum drinks!). Claire was two years older than me, but since she didn’t go to grad school, she had been in the working world for a while now. This was her chance to let loose and not have to foot the bill for it.
I rolled out of bed at 9am, which I thought was perfectly reasonable for “my” vacation celebration. It didn’t make any sense to take a shower, so I washed my face, brushed my teeth, and put on a bikini and a cover-up. On my way out of the room, I grabbed a hair clip, my sun glasses, and the book I picked up in the airport – a romance novel that Claire said her roommate really liked.
On my way to the pool, I stopped at the café for an iced coffee and a little something to eat for breakfast. Being the good sister I am, I ordered a second coffee for Claire as a thank you for getting up early to save us some seats. I strolled along the sidewalk until I finally found Claire sitting on a lounge chair right next to the bar with a perfect view of the beach.
“Glad you finally got your lazy ass out of bed…” Claire said with a smile.
“You know, I was hoping to show my appreciation for you getting up early by getting you a coffee, but maybe I will have to drink it myself!” I returned.
I set the two coffees down on the table between the two of us and settled into my chair. The warm sun felt great on my skin, and I planned to get a little bit of sun before putting sunscreen on. I wanted to get a little bit of color, but I also didn’t want to look like a lobster. Claire said something about needing to go back to the room for something, but I was content with my coffee and my book so I didn’t really pay attention to what she said.
The book I was reading was about a man whose wife dies in a car accident less than a year after their wedding. After her death, he goes on a quest to find peace with everything, and ends up meeting a woman very similar to his wife on this small island in the Florida Keys.
After about the third chapter, I realized I never put sunscreen on, so I opened the bottle of sunscreen and started applying it to my arms, legs, chest, and the rest of my body. Unfortunately, Claire wasn’t here, and I couldn’t reach my back on my own. I scanned the pool for someone who might be able to help, but most of the chairs were empty except for a few old guys playing cards and a couple of families. I was going to give up and wait for Claire, but I saw the man a couple of chairs over from me had just finished putting sunscreen on his wife and kid before they ran off to the beach.
“I’m an adult woman now,” I thought. “I can ask someone for help with sunscreen without it being weird, right.”
“Excuse me, I hate to bother you, but I was wondering if you might be able to help me with sunscreen on my back. My sister went back up to our room and is taking forever to get back,” I asked with shaky confidence.
“Ummm… Yeah, I guess I can help you,” the man said as he looked over his shoulder to see if his wife could see.
“Thanks! I really appreciate it! My name is Emily, by the way,” I said as I handed him the sunscreen and turned around.
“My name is Charles, nice to meet you,” he said as he opened the bottle.
Without thinking, I slid the straps of my bikini down along my shoulders so that he could get all of my back. His warm hands felt soft but firm on my back as he rubbed the lotion in. I couldn’t tell if he was applying sunscreen or trying to give me a massage! Either way, I wasn’t going to tell him to stop.
After a minute or two of him rubbing lotion into my back, I heard Claire’s voice. “Hey, that’s my job!” She scampered up to us. “Emily, who is your friend here?” she said with interest.
“Claire, this is Charles. Charles, this is my sister, Claire. She is the one who said she’d be right back to help with my sun lotion, but instead left me to look as red as a tomato,” I said, teasing her.
“Nice to meet you,” Charles said. “I guess now that your sister is here, you don’t need me anymore, Emily. I hope you enjoy your vacation.”
“Very nice to meet you too, Charles,” I said flirtingly. “I hope you have a nice vacation too. Maybe we’ll see each other around.”
—–
The next day, I volunteered to go reserve chairs so that Claire could sleep in. I left my room shortly after 8am, and as I was leaving, I saw Charles walking down the hall with two coffees in a carrier in one hand and a bag of food from the resort bakery.
“How nice of you to bring me breakfast!” I said with a giggle.
“Haha… I think you’ll have to get your own. These are already spoken for,” Charles responded with a smile.
Charles pulled his room key out of his pocket and unlocked the room across the hall from mine.
“Looks like I know exactly where to go if I need someone to rub my back today,” I said as I gave him a mischievous look.
“I guess so… Enjoy the pool!” Charles said as he walked into his room.
I walked down the hallway to the elevator to go claim our chairs for the day…
—–
I managed to claim the same chairs Claire had the day before. Ready for another relaxing day, I took my coverup off and lay down on my towel. I was anxious to get back to my book. I didn’t realize it would be as sexual as it was when Claire recommended it to me. The last chapter I was reading the day before ended with the two main characters having passionate sex on the beach when he said his late wife’s name. I was looking forward to seeing if it was the end of their relationship or if it would continue.
After a few chapters of reading, it was already a little after 11am, and since the bar was now open, I thought I could use a drink and a little bit of shade, so I walked over to an empty stool closest to our chairs.
“Could I have a rum punch with an extra rum floater, please?” I said to the bartender.
We had been good customers – and good tippers – the day before, and my drink arrived in short order. I sat with my back against the bar and watched the other resort guests fill out the remaining chairs at the pool.
I looked across the water and saw Charles sitting in a lounger in his red swim trunks, drinking a bottle of water. When I saw him the day before, it hadn’t really registered in my mind how good looking he was. Unlike most of the “boys” my age, he wasn’t a chiseled kind of muscular that showed he spent way too much time in the gym. He was a natural kind of muscular like he was used to doing work around his house or regularly played recreational sports with his buddies after work. Charles was looking around the pool casually when he smiled at me. I couldn’t see his eyes through his sunglasses, but I could tell who that grin was for.
If men felt the right to stare at me as I lounge around the pool, surely there wasn’t anything wrong with me staring at him.
“Some men have to be like a good wine, reaching their peak as they mature a little bit,” I thought.
Charles stood up from his chair and mentioned something to his wife before walking over to the bar.
“Hi Emily, having a good morning?” he asked politely.
“I am now,” I said.
“Could I please have a rum and coke?” Charles asked the bartender.
“Why don’t you make that a double and put it on my tab,” I said to the bartender.
“You don’t have to do that. I appreciate the offer, but I can afford my own drinks,” he said to me.
The bartender paused as if waiting for one of us to win the argument and give him the go-ahead.
“I know you can afford it, but so can I,” I responded authoritatively with a nod to the bartender. I didn’t know where this confidence came from, but it was exhilarating!
“Well, thank you, Emily,” he said, conceding to my wishes.
“I had to find some way to repay you for helping me out yesterday,” I said.
Charles grabbed his drink from the bar and raised his glass to mine.
“Cheers!” he said as he took a sip. “Damn, that’s strong!” he said before thanking me and starting to walk away.
“Hopefully that will help you relax and enjoy yourself a little bit more today,” I said with a wink.
The alcohol and the sexy book on the beach had me feeling more relaxed and flirty. I knew nothing was going to come of it, so what was the harm in fantasizing a little bit?
Having finished my drink, I ordered another and went back to my chair to read my book. By 1:30, I was feeling very tipsy from the rum and very turned on by the plot of the book. I decided to go back up to the room to get a hair clip so that I could get in the pool without getting my hair wet.
“Claire, can you keep our chairs while I go up to the room for a little while?” I asked.
“Do I look like I’m going anywhere?” she sarcastically responded.
—–
After having decided to cool off in the room for about 15 minutes, I grabbed my sunglasses, my hair clip, and the bottle of sunscreen, and I opened the door to head back to the pool. As if carefully choreographed, Charles stepped out of his room wearing only his swim trunks with a towel thrown over his shoulder and sunglasses on his head.
“Hey there, neighbor! Would you be able to help me with something?” I said without fully thinking where I was going.
“What do you need?” he said.
“Well, I got a little bit of sun yesterday, and I was hoping that you could help me with my sunscreen before I head back down to the pool,” I said, reopening the door to my room and walking back in.
Charles didn’t wait for me to invite him inside. He could read my body language.
“Isn’t that something your sister can help you do?” he said as the door closed behind him.
“Well, I might have misled you a little when I asked you for help…” I said.
Charles stood there dumbfounded as I reached behind my back and untied my top, letting it fall to the ground.
“What I really wanted help with – that’s something I don’t think my sister is really able to help with,” I said seductively as I walked toward him. I placed my hand on his chest, pushing him up against the door as I started to kiss him.
I could taste the rum on his breath – hopefully it had lowered his inhibition enough.
He pulled my body against his. As he placed his hands on my hips, I noticed that his hands were strong but surprisingly soft.
My nipples were hard with excitement feeling his body pressing against mine. As we kissed, I felt his swim trunks pressing against my body more and more firmly. Clearly he was getting just as excited as I was.
I ran my hands down the side of his body to his waistband. Tucking my thumbs inside, I slowly started to pull his swimsuit down – careful not to let his cock free yet.
Clearly distracted by my hands, Charles had stopped kissing me – his brain overloaded with anticipation. I started kissing his chest, working my way downward.
As I kneeled before him, I pulled his shorts off the rest of the way. “I’ve wanted to know what this looked like ever since you massaged my shoulders yesterday,” I said as I wrapped my left hand around his member and looked up at him. I kissed the tip of his cock as I untied the bottoms of my bikini.
“Oh fuck,” he said, clearly not anticipating what I was doing.
My lips parted open as I took his now rock-hard cock into my mouth. He was bigger than my last boyfriend, but not too big that I couldn’t fit most of it in my mouth. I slid my lips up and down his cock and delighted in the moans I was hearing him make.
Not able to resist, I slid my right hand between my legs. My pussy was swollen and wet with arousal. I wanted to be touched, but half of the excitement was the forbidden nature of having married cock in my mouth. The taste of sweat combined with the rum on my breath was a delicious combination.
Charles continued to moan as he grabbed the back of my head. I didn’t know whether he was going to shove my head on his cock and cum down my throat or what he had in mind. The bottom line was that I didn’t really care at that point.
I continued to touch my pussy, pleasuring myself as I pleasured him, when I felt his hands pull my head off of his cock, my mouth making a sucking sound as I let go of him with my lips.
“I’m not sure what you expect, but where I was raised, it was always ‘ladies first,’” he said as he picked me up off of the ground and set me on the cold granite counter and pushed me on my back. The feeling of the cold hard stone on my back was exhilarating. His lips kissed the inside of my thigh, slowly approaching my lips before retreating to the inside of my other thigh and approaching me even closer. I had never come so close to orgasm without being touched directly.
After squirming and chasing his tongue with my hips, I felt his tongue make contact with the bottom of my opening. This wasn’t his first time going down on a woman. He was good. I had never had better from a man. I rocked my hips into his tongue as he thrust his tongue into me while somehow simultaneously stimulating my clit. The heat inside of me started to build. I tried to keep quiet, but I couldn’t. The pleasure was too great as he fucked my pussy with his tongue.
I grabbed the back of his head and pushed it harder in between my thighs.
“Yes!” I moaned. “Yes! Keep going.”
I screamed in pleasure as I came.
His tongue still continued its rhythmic pattern as my body tensed and my hands clamped his mouth onto me.
“Fuck,” I said as I momentarily came down from my orgasmic high.
Charles picked me up off the counter. I placed my arms around his head as his hands held me in the air by my hips.
Charles looked me in the eye as if to ask my consent as he held me suspended above his cock.
“Fuck me, Charles,” I said, frustrated with his hesitation.
The tip of his cock paused at the entrance of my pussy.
I was more than ready for him. As he started to lower me onto his cock, I felt him pause and lift me up, then lower me down a little bit more, until I was fully impaled onto him.
I didn’t remember him being this large when he was in my mouth but he felt so good – just a little bit bigger than I had ever had before.
He pushed my back up against the wall as he fucked me.
His cock seemed to feel better with every thrust inside of me. I clenched my muscles around him, trying to squeeze him tighter.
I could tell he was getting close…
“Cum, Charles… Cum inside me. Fill my pussy…”
He couldn’t last any longer. With one last thrust and a loud grunt, he pushed me up against the wall hard and his cock tensed inside of me, shooting his load with each spasm.
I didn’t expect to orgasm again but as my body was pressed against the wall, I let out another scream of pleasure until the combination of my orgasm and being pressed against the wall made me run out of breath.
We stood there for several minutes, panting in pleasure.
Charles kissed me and lifted me off of his cock.
“So I’m curious if you still wanted me to put sunscreen on your back before I leave, or if that was just a clever ruse to get me into your room?” he said with a smile.
“I think that’s something my sister can actually help me with,” I said as I kissed him and handed him his swim trunks.
I stood there naked, leaning against the island as I watched him get dressed.
Charles looked at me with a calm face and said, “I want you to know that you don’t have to worry about getting pregnant. I had a vasectomy a few years ago…”
“Thanks for telling me,” I said with a smile and a giggle. That wasn’t at the top of my mind at the moment, but I’m sure getting pregnant would be something that would have worried me once I sobered up.
I looked through the peephole before opening the door. I didn’t want to cause him any trouble, after all.
Seeing no one outside the door, I opened it to let him out, careful not to reveal my naked body to anyone down the hall.
“Hope you enjoy the rest of your afternoon,” I said.
“I think my afternoon has already hit its high point, but you too, Emily,” he said as I closed the door.
—–
I picked my top up off of the floor and put it back on. I walked back out to my balcony to wait and watch Charles go back down to the pool.
As I waited, I ran my fingers along the lips of my pussy, feeling his cum drip out of me. The idea of a near risk-free fuck started sounding like something I could get used to. “Maybe I’ll need to find another reason for him to come over,” I said aloud to myself.
His wife and kid were in the pool, and he immediately dove into the pool to join them. I hadn’t seen him in the pool like that yet. Maybe he was in a good mood or maybe he just needed to wash the smell of sex off of him.
I put my bottoms back on and straightened up my hair before going back downstairs to Claire. “I wonder if I should tell her about Charles?” I thought. “She’ll probably try to steal him from me if I do,” I laughed to myself.
“I’m really glad Daddy got me and Claire our own room on a different floor this trip,” I said to myself as I walked out of the room smiling.
