I was sitting by the pool waiting for my sister Emily to come back. “What could be taking her so long?” I thought to myself.
I really didn’t care that much about my sister’s company at the moment – I had a drink, a seat in the sun, and several attractive men to watch around the pool – but I was about to need to get in the pool to cool off, and I was hoping Emily would bring a hair clip back for me too.
I was about to say “to hell with waiting” when I saw Emily come walking down the sidewalk toward the pool. She had a mischievous smile on her face as she walked toward me.
“What are you smiling about?” I said inquisitively.
“Oh, nothing…” Emily responded as if prompting me to ask her more questions.
“Nothing, huh?” I asked.
“Something tells me that you’ve got a fantastic story to tell me, but that you’re going to make me pry it out of you…” I continued.
“You know me all too well, Claire…” Emily responded, leaving the door open for more questions.
“Emily, quit playing games with me! Tell me!” I responded emphatically.
“If I tell you, can you promise that you aren’t going to do something to turn this into a competition?” Emily asked with a mildly concerned voice.
“You know I can’t promise that. In fact, I can all but promise that I will turn it into a competition,” I said with a devilish smile.
“Dammit, fine! I’ll tell you, BUT you have to promise that if you do turn this into a competition, you will share every detail with me too. Deal?” she asked.
“I guess that’s a reasonable compromise then,” I responded, anxiously awaiting what Emily was about to tell me.
“Do you remember my friend, Charles? You know, the one who had to put sunscreen on my back because you were too busy doing God knows what?” Emily asked.
“Yeah, I remember him,” I said, prompting her to go on.
“Well, I was walking out of our room about an hour ago, when he just so happened to step out of his room at the same exact time. Feeling a little bit tipsy and a little bit horny, I asked him if he wouldn’t mind putting some sunscreen on my back before I went back down to the pool…” she paused.
“AND?” I blurted out.
“There are a lot of details that I’m sure you don’t care about, but let’s just say that his cum is dripping out of my pussy right now,” my little sister explained.
“What. The. Fuck.” I said.
By now, Emily had somewhat discreetly covered her lower half with a towel and was now pulling her hand out from under it. She showed me her middle finger, wet with a white cream that I could only assume was proof of her adventure. “Don’t believe me? You can taste…” she offered.
“I’m good,” I said with a laugh, and I watched her clean her finger with her own lips.
“When did you turn into such a slut, Em?” I asked. “You have to tell me the rest of the story. I want to hear every detail!”
“Why do you have to hear EVERY detail, Claire? Can’t you just leave some things to your imagination?” she asked.
“I could leave those things to my imagination, but if I did, I wouldn’t know what I had to do to turn this into a competition I’m going to win,” I said with a mischievous grin.
As Emily proceeded to tell me every detail of borrowing Charles from his wife this afternoon, I watched him lounging by the pool with his wife. “How the hell am I going to top that?” I thought to myself.
“Waiter!” I told the hot server about my age. “Sex on the beach, please?” I asked in a sexy voice, intentionally being a tease.
“Uhhh… Yes… Yes, of course. Would you like a single or a double?” he asked.
“I’ll take a double, please,” I said with a smile.
I sat in my lounge chair for another couple of hours, watching the man my little sister just fucked, enjoying a nice vacation with his family, wanting to prove to Emily that I’m still the more talented sister.
—–
For dinner that night, Emily and I went to a beachside restaurant with Mom and Dad. Emily was her normal cheerful self, but I could not help but be distracted thinking about my younger sister getting fucked in our room by Charles.
“What’s on your mind, Claire? You seem distracted,” Dad asked.
“Huh? Oh, nothing,” I responded confusedly.
“I was just thinking about something Emily mentioned earlier today, and all the things I want to do before our vacation is over,” I vaguely answered the question.
“Thanks again for these vacations, Daddy! It’s great to spend time together even though we’re all grown up now,” I said.
“You’re welcome, sweetheart! I am just glad you girls finally get along so well. Do you remember that one time when you were a Junior in high school and the two of you were fighting over a boy you met at the beach?” Dad said, reminiscing fondly over past vacations.
Emily jumped in before I could respond, “You are so right, Daddy. Claire and I have put those days of vacation competitions over boys behind us.”
I felt Emily’s foot tap the top of mine as she said it. If he knew that a random middle-aged married man had just fucked his daughter, this would be the last vacation he ever paid for. Thankfully, Emily and I have gotten a little bit more discreet in our mischief over the years.
—–
The next morning, Emily and I repeated our daily ritual: iced coffees by the pool in the morning, followed by drinks as soon as the bar opened at 11 am. By 3:00 in the afternoon, Emily and I were both feeling more than tipsy, and I decided I had more than enough to lower any inhibitions about going after Emily’s “sloppy seconds.”
I had been casually watching him throughout the afternoon, just waiting for the right opportunity to get him alone. I saw him put on his shirt, grab his towel and beer, and head for the elevator back up to our floor. His wife and kid were still down at the pool, and they had enough stuff that I was reasonably certain that I wouldn’t have to worry about anyone interrupting us.
“This will be the perfect opportunity,” I thought confidently.
Charles made it onto the elevator before I could catch up, so my plan was going to have to change.
When I got up to our room, I quickly took off my bikini and hopped in the shower to rinse off my body. I didn’t have time for a full shower, but I wanted to rinse off the sweat and sunscreen a little bit at least. I skipped panties and a bra and slid on my favorite floral sundress, but I intentionally didn’t button the back. That would be a job for Charles.
I walked to the door, thinking I could invite Charles into our room to button my dress and fuck him just like Emily. “Men are simple, right? I’m sure he’ll fall for the same trap Emily laid for him.”
I stepped into the hallway and knocked on the door across from ours. This was it…
“Hello?” a woman answered the door… it was his wife.
A thousand thoughts rushed through my mind in a split second…
“Did she know what Emily did?”
“How do I make it seem like I wasn’t just looking for her husband?”
“I really hate to bother you… But I was just wondering if you could help me button my dress?” I timidly asked. “I would have asked my sister, but she’s still down at the pool.”
“Of course I can. Turn around,” she said.
As she pulled the two sides of my dress together, she muttered, “Shit.”
“I’m terribly sorry, but it looks like the button just came off,” she explained.
“Oh, that’s okay… I can wear something else; thanks for trying!” I said, anxiously hoping to retreat to our room and reevaluate my ambitions.
As the woman reached her hand out to give me the button, I realized I had forgotten both my room key and my cell phone. She could tell by the look on my face what had happened.
“Let me guess, you left your key in your room?” she laughed.
I couldn’t help but laugh back and say, “You guessed it!”
“I think I have a sewing kit in my bag if you want me to fix it for you?” she asked. “That way, you can at least be appropriately clothed to go ask the front desk for an extra key.”
“Are you sure? I don’t want to be a pain,” I responded.
“Come on in,” she said. “It will only take a minute.”
I entered their room and stood by the kitchen counter as she retrieved the sewing kit from the master bedroom.
She returned a moment later with the kit in hand and said, “I guess I should introduce myself. I’m Anna.”
“I’m Claire. Thanks for helping me out, Anna. This is extraordinarily embarrassing,” I admitted.
“Claire, go ahead and take your dress off, and I’ll get you fixed up in no time,” she said.
My eyes widened, “I’m not wearing anything under my dress…” I said softly.
Before I could say anything else, Anna said, “Don’t be embarrassed, in college, I lived with a few girls, and we had a clothing-optional kind of policy around the apartment.”
“Ummm…” my mouth muttered as my brain tried to catch up with what was happening.
“How about this? You’ll take off your dress so that I can fix it, and so that you’re not the only one, I’ll take off my swimsuit. I was about to hop in the shower anyway,” she said calmly and confidently, already undressing before I had a chance to answer.
I slipped the shoulder straps off my shoulders as Anna was already naked and waiting for me. My dress dropped to the floor, and I stood there motionless for a moment.
“Wow…” Anna said under her breath as she looked at my naked body.
We both suddenly bent down to pick up my dress so that she could fix it, and as we bent over, she said, “I’m sorry. I haven’t seen another woman naked since college, and it kinda took me back to my wilder days.”
I felt a tension between us, each hoping the other would make an advance. My mind raced… she hadn’t seen another woman naked since college? Seeing me took her back to her wilder days?
I dropped the dress and kissed her. She was clearly not anticipating that, but she didn’t pull away from me. I could feel the tension melt when she placed her hand on the back of my head.
Her lips were soft on mine; a softness that I have never had with men before.
Anna gently placed her other hand on my hip and pulled my body against her. Our legs naturally staggered between each other.
Anna’s kisses became more passionate, sliding her tongue into my mouth and then biting my lip.
I had been anticipating sex with a stranger, but this wasn’t my plan… the warmth between my legs had grown. I could feel my heart beating in my arousal, my pussy throbbing and wanting more.
“Have you ever been with a woman before?” Anna asked.
As I started to speak, she moved her hand between my legs. I spread my stance wider to invite her in. As her finger ran along the inside of my left thigh, all I could do was gently nod my head up and down as she looked into my eyes. Her fingers traced around my wet opening, but every time she got close to what I wanted, she slowly moved them away.
Anna pushed my body up against the kitchen island. The sensation of the cold granite against my ass was a shock to my nervous system, and I let out a gasp. She helped guide my body on top of the island and she pushed my shoulders to lay me down.
Anna’s soft lips kissed the insides of my thighs as her fingers continued to tease my hungry pussy.
“Go down on me, please!” I begged.
“I was hoping you would ask,” Anna said smiling.
I felt her tongue start at the bottom of my opening and slowly approach my clit.
“Yes!” I gasped.
As her tongue finally arrived at my clit, she slid her finger inside of me. It had been a long time since I had been with another woman, and I forgot how much better they can touch you than a man.
Anna continued to run her tongue across my clit as her fingers danced inside of me. Her fingers explored places inside of me that I didn’t even know could feel that good.
I didn’t have to want to orgasm, my body told me it was imminent.
Breathing hard and thrusting my hips against her hand, my body started to tighten, my back arching. “Oh, my God, yes! Yes! Anna! Keep going!” I said.
“YESSS!” I screamed as my legs clamped around her head.
She didn’t stop… her tongue kept going, her fingers thrusting.
I needed her to stop, but I couldn’t. The first wave of my orgasm transitioned into a second as I grabbed her head and pulled her mouth even harder against me.
After the peak of my second orgasm, I had to pull her head away from me. My body was tensed so tight that I couldn’t breath.
“Fuck,” I said trying to catch my breath.
I opened my eyes to see Anna standing there back against the fridge, trying to catch her breath. Her fingers were already rubbing herself as her eyes looked down on my.
“Your turn,” I said as I stood up. I grabbed her hand and lead her to the couch, which was covered in children’s swim toys – goggles, dive sticks, a rubber torpedo, among other things.
I pushed them to the side, making room for Anna to sit down.
I kneeled down in front of her, and with my eyes staring into hers, I slowly spread her legs.
My hands slid under her knees and pulled her out toward me as I lowered my lips to her. I couldn’t tease her. I had to taste her immediately.
Sliding my tongue from the bottom of her slit upward, the taste was delightful. I withdrew my tongue and repeated the motion several times until my tongue had slid at least an inch into her. I could taste the familiar flavor of cum from her pussy. I assumed Charles gave her a good fuck last night or this morning after Emily drained him a first time.
I continued flicking my tongue against her clit as I played with her nipple with one hand and slid a finger from my other hand inside of her.
“I love the taste of a woman, I love having my face buried in her pussy, and I love the taste of cum left over,” I thought to myself.
Out of the corner of my eye, I saw the rubber torpedo swim toy. It was about eight inches long – pointed at the tip, but very girthy in the middle.
I grabbed hold of it firmly and slowly slid it into Anna’s pussy.
Anna’s eyes grew wide, uncertain how to react. This was clearly more than she was expecting.
“Ahhhh,” she moaned in pleasure.
“Do you want me to stop?” I asked playfully.
“You better not, Claire,” she said strongly, lifting her hips to meet the torpedo.
I slid the toy inside her and withdrew it in a rhythmic motion, and with each thrust, I slid it inside of her further until she had taken the girthiest part.
With every thrust of the toy, she let out a moan, growing louder and starting to raise her hips up to meet my thrusts.
Suddenly, her body tightened, and as she screamed, her pussy squirted around the toy and onto my body.
Anna tried to catch her breath, but her pussy kept shaking around the large toy.
After she had caught her breath, I slowly withdrew the toy from her stretched pussy. She let out a gasp as she lay there with her legs spread in front of me, pussy gaping wide open.
“That was fucking amazing, Claire!” she said to me. “It has been years since I’ve orgasmed that hard.”
I smiled and giggled, “I guess it’s a good thing that button came off my dress.”
“I guess so,” she laughed.
She picked up the toy torpedo and looked at it, “I guess this has found another purpose now.”
Anna stood up and lifted my body into the same position on the couch that hers had occupied just moments before.
“I think it’s your turn now,” she said, kneeling between my legs.
The light glistened off the toy, a mixture of Anna’s pussy and Charles’s cum.
“I want you to fuck me, Anna,” I begged.
She positioned the tip of the toy at my already wet slit and slowly ran it up and down.
“Good, because I want to fuck you with this,” she said as she slid the cum covered toy inside of me.
The torpedo felt so good as it stretched my pussy more with each thrust. I felt like I couldn’t take much more girth when I realized it was only halfway inside of me.
I threw my head back and screamed in pleasure as Anna fucked me with the pool toy.
Bucking my hips up to meet her thrusts, I grabbed my breasts and pinched my nipples.
“Deeper, Anna! This feels amazing,” I cried.
She thrust the toy inside of me as far as it would go. I moaned in pleasure and pain as I approached my orgasm.
“Oh… OOHhh… Ahhh… Yes… fuck… me… YES… YESSS!” I screamed as my body shook in orgasm.
I could feel the redness in my face, and I could see the combination of sweat and Anna’s cum on my body.
Anna slid the toy out of me and smiled with satisfaction.
“As much fun as this has been, I’m thinking we should clean up before either my husband or your sister come back and catch us,” she said.
“What do you think your husband would do if he came back and found you with a hot twenty-something naked on your couch?” I said boldly.
“Probably the same thing I did when I found a hot, naked twenty-something naked in my kitchen,” she said, somewhat puzzled at me asking the question.
I picked up my dress and slipped it on for the walk back across the hall. Hopefully, Emily would be back by now to let me in.
“Would you like to take my sewing kit with you, Claire?” she asked.
I thanked her but politely refused. “Maybe I’ll keep this dress as a reason to come back over and ask for your sewing kit again,” I said as I kissed her goodbye.
“We will have to see what happens, but I’m thinking this is going to have to be a one-time thing,” she said regretfully. “I would hate to have Charles find out I cheated on him.”
“I understand, but life is full of surprises,” I said as I closed the door.
—–
I walked across the hall, hoping to find my sister had returned and could let me into our room. I really didn’t want to have to walk through the resort smelling of sex and wearing a sundress with a ripped button.
To my relief, Emily opened the door to let me in.
“Where the fuck have you been?” she asked as she took a closer look at me. “And what the fuck happened to you?”
“Have I got a story for you…” I said, walking into the room and closing the door behind me.
