Chapter 9

Thank you to wrc264 for your help in editing this chapter.

If you’ve been following my story, you know that my parents took me and my sister, Kelly, to a nudist family resort. It’s more than that, it’s a family sex resort. This is the tale of the last full day on the island. From my earlier writing, you know that I’ve seen parents and kids having sex. I’ve had crazy sex with my mom and sister. My sister went as far as blowing my dad and pushing his cum into my mouth when she kissed me.

Like the previous mornings, I woke up hard. The difference this time was that Kelly’s lips were over my swollen head and going up and down my shaft. The warm lips working my cock made me moan and grab the top of Kelly’s head. This caused my sister to let my cock slip from her mouth and then look up at me.

“Good, you’re awake. Let’s go. I feel like some yoga this morning.”

Kelly smiled at me as she slipped off the bed while simultaneously grabbing my hand to pull me off the bed.

“Let’s go little brother.”

“Give me a minute.” Rubbing the sleep from my eyes, I pondered another yoga lesson. I loved the idea of eating pussy early in the morning, but I wasn’t too keen on getting rimmed again.

“Let’s go!” Kelly pulled harder on my arm, nearly dragging me from the bed.

“Fine.” I surrendered the inevitable and followed my sister into the bathroom.

I watched as Kelly sat down on the toilet. She spread her legs to give me a good view of her pissing. “Do you like what you see?” Leaning back to give me an even better view, my sister smiled as she continued to pee. After a minute, she grabbed a wad of toilet paper to wipe off the remaining golden droplets clinging to her pussy lips.

I replaced my sister at the toilet, lifting the seat before peeing. I was surprised when Kelly came up behind me and started aiming my cock at the toilet. Surprisingly, my sister has pretty good aim and the flow went into the center of the bowl. It was a little painful since my sister was pressing down on my hardon. Even more surprising than my sister’s aim was the fact that she got down on her knees to suck my cock. Kelly smiled when she got off her knees. I couldn’t believe my sister licked off my dick after peeing or that she told me that she liked how it tasted.

Like the previous day, we slipped past our sleeping parents and out of the cottage. We headed to the left and started walking. My sister wondered if Robert, his wife, and daughter would be doing yoga this morning. While my little head was fully awake, the big brain was still half asleep. My little head hoped that it would soon be buried in someone’s mouth or pussy.

“I need to get fucked this morning.” Kelly smiled at me and then pulled me by the hand as she picked up the pace.

We walked around the patch of bushes and saw the family. “Good morning.” It was Wendy. Her husband said hello too. Becky smiled at both of us and licked her lips.

“Good morning.” My sister and I said at the same time. “We hope you don’t mind if we join you.” Kelly added at the end.

“Certainly. I was hoping that you two might join us again.” Robert looked at my sister and she looked at his giant cock.

“If you two want to grab some towels and lay them out, we can begin” Wendy pointed to a couple of towels.

Grabbing the towels, Kelly placed hers next to Robert, while I placed mine between mother and daughter. Bending at the waist, Kelly gave Robert a clear view of her pussy and her asshole. After what happened the previous day, it wasn’t surprising when he reached out and touched my sister’s pussy. He traced a line between her lips and ran it up to her butthole. Running his finger back down again, he sank one finger into Kelly until it was all the way inside her.

“If you two are ready over there, we can begin.” Wendy gave her husband the look. He pulled his finger out like a child who’d been caught with his hand in the cookie jar.

Like the day before, Wendy had us touching our toes and holding that position for fifteen seconds. The hand on my ass didn’t surprise me. I turned my head to the left and was eye level to the older woman’s bald pussy. A voice reminded me to focus on my breathing and try to relax. It was difficult enough relaxing with a naked pussy inches from my face, what made it nearly impossible was a finger rubbing my butthole.

We stood upright once again in Wendy’s direction. The next pose had me standing with my feet shoulder width apart as I reached my right hand over my head as my left hand tried to touch the side of my left foot. I went slowly as I got into the pose. I looked over at Becky and she was staring at my dick, which was still about semihard. I thought to myself that I’d be happy to give up the yoga class now and get straight to fucking mother and daughter.

The next set of yoga poses were like the ones the previous day. My poses had not improved, and Wendy reminded me to calm my breathing and focus and executing the poses as best I can. We did several more poses, each progressively harder. At one point, she walked in front of me and told me to stand.

“Yoga is about grace and focus Josh. Watch me.”

Wendy walked in front of me. Moving her hands slowly up the sides of her body, she reached for the sky. Slowly she bent at the waist, until she touched her toe. It’s at this point that I saw it. A pink jewel was covering Wendy’s asshole. I looked again to make certain I was seeing this correctly. Yes, Wendy had a jeweled butt plug in her asshole. I looked to my right and saw Becky bending over as well. The jewel on the end of her plug was a deep red color.

Wendy told us to stand up and then she got us into the downward dog facing position. Unlike yesterday, Wendy didn’t straddle me to hold me up. This time it was Becky standing in front of me. Like her daughter did the day before, Wendy rimmed my ass after spreading my ass cheeks apart. I moaned as a tongue played with my rim and a hand stroked my cock.”

“Oh Fuck!.”

The sound of Kelly’s cry made me turn my head. I looked just as Robert was sliding a butt plug into my sister. It looked like the jewel was a bright blue color. Another moan escaped my sister’s lips as Robert licked around her asshole.

Focused on Kelly, I didn’t feel the cold lube or the probing sensation in my ass until it was too late. I yelped a little at what I thought was Wendy’s fingers. It wasn’t a finger, but some type of probe. A jolt of electricity went up my spine as the probe touched something in my ass.

“Relax Josh, this is a prostrate massager. It may feel uncomfortable now but trust me, you’re going to have the most powerful orgasm you’ve ever had in your life. Robert has one like it in his ass. Watch.”

With that Wendy’s fingered a remote by her yoga mat and I watched Robert moan. In between his moans, he called his wife a naughty little whore.

“See Josh, he likes it. It stimulates the prostrate and makes a man cum so much harder than normal. Becky is going to let go of your hips and I want you to roll over. Then we can get started.”

“Okay...” My voice creaked as I continued to resist the probe in me.

“Relax Josh. This will be so much better if you don’t fight it. Now roll over.”

“Yes, Ma’am.” I don’t know why I was so formal in my response. It just seemed like the right thing to say to a woman who just shoved a probe up your ass and was about to have sex with you.

Rolling over. I watched as Becky’s lips wrapped around my cock and started sucking. Soft lips focused on my swollen head, licking the ring at the base of my tip. Her tongue swirled around the head. After several swirls, she’d take half my cock down her throat and then repeat it once again.

I lost sight of Becky as Wendy planted her pussy on my face. A sweet aroma filled my nose as my tongue thrust upwards into wet flesh. Dripping already, the older woman tasted like she’d already been fucked this morning. I’d been fed cum by my sister and mother, so I had an idea what it tastes like.

‘FUUUUUUUUU.” The words wouldn’t come out since my mouth was pressed into a pussy. It felt like a bolt of lightning hit my body. The point of impact of the punch came from my ass. More precisely, it came from my plug in my ass vibrating against my insides. Grabbing Becky’s head, I thrust my cock deeper into her throat.

“That’s it Josh, ride the wave.”

The vibrations in my ass went on for a minute. The thrusts into Becky’s mouth continued as well. Then it suddenly stopped, and Wendy climbed off my face. My breathing was hard, and I tried to catch my breath.

Wendy looked over at her husband and told him to pull out of Kelly. She then offered me a hand to stand up. Once I stood up, Becky took me by the hand and led me towards their cabin and the beach bed. About halfway there, a low vibration started pulsating out from the toy. Robert and I both looked at his wife who just smiled and held up both remotes.

Once we’d arrived at their cottage, Becky grabbed Kelly’s hand, and both fell backwards with their legs spread wide open. Robert walked to my sister and sank his thick shaft into her. Kelly moaned and begged the dad to fuck her senseless.

Wendy walked over to me and placed her hand on my ass. Her fingers found the toy shoved up my ass and pressed it in a little farther. She rotated it from left to right by moving the part outside of my butt.

“I want you to fuck my daughter’s tight little cunt and cum in it for me.”

I looked at her. “Yes ma’am.”

Not wasting any time, I walked over to the sunbed and plunged my raging hardon into the young woman. The vibrations in my ass made it hard to focus at first. I tried to think about how tight Becky is, hoping that I could concentrate on that.

What eventually shifted my focus was not Becky’s pussy, but Wendy. She climbed up on Becky’s face and started grinding her pussy on it. Watching a daughter eat her mother out sent a chill up my spine. I kept thrusting into Becky, even as the first orgasm rocked her body.

My attention focused once again on the vibrator in my ass as I watched Wendy hold up both the remotes and press a button on each. The intensity of the vibrations increased.

“Doesn’t my daughter have the tightest little cunt?” Wendy looked at me. “I’m thinking of letting the guys that come to my yoga studio fuck her. She likes to come to my classes sometimes and teases them by wearing tiny little yoga shorts.”

I kept thrusting into Becky as the intensity again ramped upwards.

“I bet each one would pay good money to see her do naked hot yoga. Then when they’re all hard, I’d pick the ones with the biggest cocks to seed her little fuck hole.”

Wendy told me to fuck Becky harder and faster.

“I bet more than a few of my female students would love to eat the cum out of her dripping pussy.”

The vibrations increased. Thrusting deeper into Becky, her pussy explode in a waterfall of liquid. Her mother saw it as well.

“That’s it baby, squirt for mommy.”

Wet inner thighs shifted the focus from the toy in my ass to Becky’s pussy. I kept thrusting, letting her tight hole grip my shaft.

“FUUUUUCCCCCK”

Robert cried out and so did my sister. He was thrusting deliberately deep and slow into my sister. He was cumming in her.

The vibrations in my ass reached a fever pitch. Each thrust into Becky brought me that much closer to the edge. Wendy climbed off her daughter and came up behind me. I felt her hand on my ass as she helped me press deeper into her daughter.

“When you cum Josh it will feel like you are being electrocuted. Keep thrusting into her and only pull out once your balls are empty.”

I kept thrusting into Becky. I didn’t see Wendy press the remote button, but I felt it. The vibrator in my ass took off faster than a stock car. Wendy yelled for me to go faster. Becky moaned, grabbing my arms that were on either side of her rib cages.

“FUUUUUUUCCCCCK” I screamed.

Wendy was right, it did feel like I was being hit with a bolt of lightning. My toes curled in the sand and my knees felt weak as I blasted a firehose of seed deep into Becky. The second stream was just as powerful as the first. Becky wrapped her legs around my waist and begged me to fill her up. I was in heaven as the most powerful orgasm of my life pushed more and more cum deep into the young woman. I kept thrusting into her long after my balls were empty.

Wendy helped Becky unwrap her legs from my waist. Then she pulled me out, pushing me off to the side. The MILF then dove face first into her daughter’s soiled pussy. Robert and I watched as Kelly climbed onto Becky’s face. I watched as the young girl ate her father’s cum out of my sister’s pussy.

Robert walked over to where his daughter was being eaten and grabbed the remotes to the toys. He handed one to me and told me how to stop the toy. I pressed the wrong button, and the pulsating vibrations made me moan once more. I pressed another button and the vibrations stopped.

Robert then handed me a towel and told me to pull the toy out of my ass. While the vibrations were bad, the toy slipping out of my ass was a little more painful. My anal ring was once again stretched as the widest part of the toy was pulled from my ass. Thankfully, it lasted only a moment, and I dropped the toy on the towel after I’d wiped off the lube from my butt.

Robert and I watched the three women eat and lick each other. We’d recovered and were starting to get hard once again by the time that three women were pulling themselves apart. I took a go at Wendy, ramming my cock down her throat as her husband buried his monster cock in her pussy. We must have fucked for another twenty minutes before I exploded once again, pumping seed down Wendy’s throat.

After we pulled ourselves apart, Robert asked if we were heading to breakfast. Kelly and I looked at each other and shook our heads. My sister mentioned that we needed to wake up our parents. Wendy said that we should all go to breakfast together and that would be the chance to meet our mom and dad.

Robert asked me to help gather up the yoga equipment while the girls went to fix their hair and brush their teeth. As we walked down to the beach, he asked me what I thought about the prostate massage. This started a conversation about prostate milking and sex. This was by far the strangest conversation I’ve ever had. Wendy did this to Robert on a frequent basis and that his daughter was learning to do it as well.

Wendy, Becky, and Kelly were ready to head over to our cottage by the time we put away the yoga equipment. We started walking and talking about the day. Robert asked if we’d heard anything about the pool dance party happening tonight. We said that we hadn’t and that we could ask the front desk after breakfast.

We arrived at our cabin a few minutes later and found it empty. I looked over at Sam’s cabin and it too looked empty. Kelly said that it was likely that our parents had already gone over to the restaurant.

Our parents were indeed at the restaurant. My mom and Clair were talking, and we joined them at the round table next to them. It was Kelly’s idea to sit with Robert, Wendy, and Becky. She whispered that we didn’t want them to feel left out since there wasn’t enough room for everyone to sit at one table.

Eventually, the kids decided to switch places, so we were all together and the adults were sitting at one table and the kids were at the other. I sat between Kelly and Sam. Becky placed herself between Sam’s twin brothers. The twins were telling Becky about themselves and flirting.

Sam’s hand found my cock under that table. She smiled at me and whispered in my ear how pretty Becky is. When I blushed, she whispered in my ear again. This time she asked me if I liked fucking Becky. I was going to deny it and then Sam squeezed my dick. My blushing gave my secret away and there was no denying I’d done it earlier this morning. I just smiled at Sam and said that she and Becky can have me any time they want.

We finished eating and headed over to the front desk. We found Sue checking out a few guests who were dressed and had their luggage with them. Once Sue finished with them, my dad asked about the ferry to the mainland. We were told the first ferry leaves at nine in the morning. Robert said that he’d heard there is a pool party tonight and asked what time it starts. The smile on Sues face was wide as she said there will be games and a pool party and that it starts at eight in the evening.

My folks said that we will be going. Sue looked at all of us and said that she hopes that we’ll take part in the games as well. My parents invited Robert and Wendy to hang out at the beach with us. They said yes and that they needed to pick up some supplies from their cabin and that they would meet us in thirty minutes.

Sam interlaced her fingers with mine as we walked back to the cabin. No words were spoken, but the grip on my hand was tight. I got the feeling that there was a hint of jealousy coming from Sam towards Becky.

Becky and her parents arrived just as my mom was finishing applying sunscreen to my hard cock. We all headed to the water and started playing frisbee. We played games in the water and swam for a few hours. The budding rivalry between Sam and Becky manifested itself more when the new girl set her sights on the twins.

Our parents went and grabbed food from the restaurant for us since we were into the third quarter of a football game. The twins and Becky were beating Sam, Kelly, and I by seven points when our parents headed off to the restaurant. Thankfully, our moms brought us sandwiches, chips, and sodas. We called a time out to gulp down food before finishing the game. In the end, we lost to the twins by a touchdown.

I don’t think anyone remembers the moment they fell asleep and I certainly didn’t know when I drifted off. I must have slept hard since I didn’t hear when it started. When I finally opened my eyes, my mom and Claire were getting fucked my Robert. My dad and Sam’s dad were spit roasting Wendy. The twins had Becky in a similar position. My sister and Sam were quietly licking each other’s pussy. I closed my eyes and focused on the sound of my family fucking.

It was around four o’clock, when my sister pulled her face from Sam’s crotch. She told me to open my eyes and that she’s know that I’ve been awake for a while. It was then that I heard my dad as he nutted into Wendy and pulled out. Sam’s dad had already shot his load into the MILF. Claire was getting her second load of Robert’s cum. The twins had pulled out of Becky after DP’ing her and cumming in her pussy and ass.

Claire said something about being hungry and wondered if it was too early to eat. Everyone agreed that grabbing an early dinner would be good since they didn’t want to feel too full during the pool party. Like earlier in the morning, the kids took one table while the adults sat at another. The seating arrangement was identical as my sister and Sam sat on either side of me.

While we ate, Sam asked us if we’d heard about the games that we’d be playing tonight. Everyone said that we didn’t know and that we would soon find out. As we ate, Sam asked about the next stage of our trip. Kelly mentioned that our next stop is Greece. She said that we’d be going to a few nude beaches in Europe. My sister named off a few more places that we’d be visiting.

It was almost six in the evening when we left the restaurant. My parents pulled us by the hand and said that we needed to go back to our cabin and that we’d meet everyone at the pool. Once back in the cabin, our parents talked to us about the party and that we couldn’t stay out too late. They then told us that we need to set out our clothes for our trip tomorrow and at what time we need to be ready for breakfast and to head to the dock.

I thought the directions were pointless since I really didn’t have to pack anything. I’ve been naked for the last week and didn’t have any clothes to pack. My mom mentioned that I should pull out a fresh set of clothes since the ones I flew here with might be a little stinky. It took me less than ten minutes to lay out new clothes, pack the old stuff and shove my tablet and phone in my carry on. My sister finished about the same time as me. We waited on the couch for our parents to finish.

It was about seven when we left the cottage and headed over to the pool. There were families milling around and we walked over too where Sam and Becky were talking to their parents. The twins were on the other side of the pool talking to Elsa and her older sister.

Out of the corner of my eye I saw our housekeeper setting up the party. We made eye contact and I waved at her. Just then Kemry came up and caught me waving. She waved back at me along with Maria. I wondered if Kemry and Maria would be up for a threesome. I continued to watch Kemry and her mother, ignoring the conversation between my sister and Sam.

It was almost eight when the crowd started to gather at the pool. Sue grabbed the microphone from her husband as her children stood by her side.

“Welcome everyone. On behalf of my family and my husband’s brother and his family, I’d like to thank you for staying at our resort. We dreamed of a place where families can be free to grow closer to each other. Some of you have been here for several days and hopefully bonded with your family as well as made new friends. A few of you just arrived today and we welcome you. For those of you that haven’t been here before, Friday night is game night here at the resort. After game night, we’ll have the house DJ play some music and we’ll turn on the foam machine.

“We have a couple of games for families, but not your typical games. These are interactive games. So, who wants to play a game?”

The crowd cheered.

“For the first game we are going to need the fathers and daughters to pair up. Dads, come on over and print your names on a slip of paper and put them into the hat.”

We watched as the dads walked over to the table and started scribbling names on a piece of paper. Out of the corner of my eye, I noticed the staff moving three of the sunbeds closer to each other. Then they set up a contraption that had sheets attached to it. It looked like they were setting up some type of puppet show.

With all the names of the dads and daughters in the top hat, Sue got everyone’s attention. “Are there any dads and daughters that still need to sign up?” Waiting a second, she continued. “Good. Now we are going to draw five names from the hat.”

Sue drew out five names, calling each dad and daughter up to stand by her. Robert and Becky were called. You could see the look of disappointment on Kelly’s and Sam’s faces.

“Now that we have all five of our contestants, we are going to play a game called ‘Who’s your daddy.’ The goal of the game is for daughter’s to figure out who is their father without looking at them. Girls, if you will make your way over to the beds, the staff will help you get ready.”

We watched as the girls went over to the sunbeds. They were instructed to climb onto the sunbeds on their hands and knees with their asses near the end. Each was given a blindfold and told to put them on. The staff draped the sheets over their bodies, hiding their upper torso and heads from the view of the audience.

“Now dads, you are going to have ninety seconds with each of the daughters. You can only touch them with your tongue, or your dick. You’re not allowed to speak to them or grab them with your hands. The goal of the game is for your daughter to be able to pick you out from the other dads.”

A few of the young women on the sunbeds squealed their excitement when they heard they were going to get fucked by five different guys. I was certain that Becky and her dad would win given how big his cock is and how she responded to him fucking her the other day.

“Now dads, we are going to hand you a number card and we need you to hold that up so the staff member can tell the girls which contestant is with her.”

We watched as Kemry handed the number cards to the dads.

“We are about to begin. If you need some help getting hard, Kemry has happily offered her mouth.

I watched as Kemry walked over to the first dad and dropped to her knees. She grabbed his cock and leaned forward, letting the semihard flesh slip between her lips. The young girl started bobbing her mouth up and down on the cock, making slurping sounds.

Sue didn’t mention this when she explained the game, but the five female staff members walked up behind the girls and kneeled. Each buried their face in the young woman’s ass licking their pussies.

I felt my fingers intertwine with someone’s else’s fingers. It was Sam. “Damn, she’s lucky.”

I looked at her. “Would you rather suck five cocks, or get fucked by them?”

“Can I do both?” Sam smiled at me.

By this point the first dad was hard and he pulled out of Kemry’s mouth. The crowd watched as the first staff member got off her knees and walked to the other end of the sunbed. The dad walked over to the first girl on the bed. The staff member on the other side of the sheet said something to the young woman and then gave the dad the thumbs up. The dad grabbed his cock and aimed it at the naked pussy. He bottomed out in one stroke as the girl moaned.

The timer started and the second dad walked up to Kemry. She eagerly swallowed his hard cock and started slurping his dick as her head bobbed up and down. Thirty seconds passed and the girl on the bed was moaning.

When the time hit sixty second, Sue called out that there were 30 seconds left. That was the signal for the staff member eating out the second young woman to get off her knees and walk to the head of the sunbed next to the second contestant. Kemry let the dad’s dick pop out of her mouth and the second dad walked over to the bed.

“Time.” Sue said it loud enough for everyone near the pool to heat it.

The first dad pulled out his cock and walked over to the second young girl. The staff members said something to the woman and then gave both dads the thumbs up. Each plunged their dick into the pussy in front of them. They both bottomed out, slapping their flesh against the tight young asses in front of them.

Sam squeezed my hand. She said how she wants to get fucked by an anonymous guy. We both watched as the cycle repeated. The third dad took his place in front of Kemry. She eagerly gobbled his cock, bobbing her head back and forth. Drool escaped from her lips as she took more of his hardon.

The two women on the bed moaned as faceless cocks slammed into their pussies. The first girl was moaning louder than the second one. Taking a second faceless cock, she called out when the first orgasm hit her.

Kemry grabbed the third dad’s cock and was licking the underside before bobbing her head up and down on the swollen head. Her hands her going along the length of his shaft, keeping perfect rhythm with the up and down movement of her mouth.

Sam squeezed my hand harder as Sue called out once again that sixty seconds had passed. Like before we watched as the third staff member dislodge her mouth from the bald pussy of the young woman and walk to the head of the sunbed.

Like before, Kemry let the older man’s cock slip from her mouth and nudged the dad to walk over to the first young girl. At ninety seconds, Sue called time and the first two dads pulled their dicks out and moved down the line. A whisper to the girls and a thumbs up and the cycle started again.

The fourth dad was rock hard when he walked in front of Kemry to offer her his dick. Sam and I watched as Kemry closed her eyes and started trying to deep throat the guy. She was able to get most of his dick down her throat after grabbing his ass and pulling her face towards the root of his shaft. Sam and I were so enthralled watching Kemry that we missed how the three dads were fucking the girls.

The sound of Sue’s voice calling out the time drew us away from Kemry and towards the moaning girls. At the appointed time, the staff member pulled her face away from the girl and walked to the head of the bed. The fourth dad took his place and when time was called, the men shifted and each soon had their shaft buried in a young woman.

Sam commented on Robert’s massive dick. If by design or happenstance, the dad with the biggest dick was left for last. We watched as Kemry wrapped both hands around his thick shaft as she bobbed her lips down the first three or so inches of it. Using both hands, she pumped his veined shaft. The struggle to take as much of Robert’s cock in her mouth ended sixty seconds later as Kemry’s mom called out the time.

Robert walked over to the first girl and at the appointed time the dad’s pulled out and switched places. With the word from Sue, all five dads plunged their dicks into the girls. The first one to take Robert’s dick cried out as he split her open.

The moans of young women filled the silence by the pool. I looked over and saw Elsa a few yards from me. She was stroking her father’s cock with one hand and playing with her mom’s pussy with the other. I hadn’t noticed it before, but the fingers of Sam’s free hand were dancing across her clit.

Time was called again and the dad’s pulled out and switched spots. It’s at that point the staff member at the head of the bed asked the first young girl something and then took a pen out and wrote on a piece of paper. The staff member then walked back to the foot of the bed and resumed eating the pussy of the first contestant.