Chapter 8

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

If you are new to my story, let me introduce myself. I’m Josh Greysen. I’m sixteen years old and the younger of two children. My sister Kelly is eighteen and just graduated from high school. My parents, Jeffrey, and Amy promised my sister a trip to Europe as a graduation gift. About a month before we were supposed to go on vacation, our parents informed us that we were adding to our holiday plans with a trip to a nudist family resort. What follows is more of my adventures at the resort.

Begin Story

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 actually, it’s a family sex resort. Over the last several days, I’ve seen parents and kids having sex. I’ve had 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. This is what the second to last full day on the island was like.

Like the previous days, my cock was up before me or the sun. I’m not certain if I woke from the sun starting to peak over the horizon or the fingertips that were playing with the rim of my swollen cock head. I opened my eyes to see my sister’s face right next to mine. Leaning in to kiss me, I felt her fingers wrap around my engorged cock.

Soft lips pressed against mine and I opened my mouth, allowing Kelly’s tongue to press against my own. The kiss lasted only a few seconds and our lips parted.

“Good morning.” My sister said in a hushed voice. “Let’s get up. Mom and dad are still sleeping.”

“Okay.” I was still half asleep.

“Let’s go outside so we can have fun like yesterday.” Kelly showed all of her bright white teeth when she smiled at me.

“Okay, fine. I’m getting up.”

My sister and I climbed out of the bed, tiptoeing past our parents room. They were sound asleep with both of them breathing heavily, but not snoring. A quick stop at the bathroom to pee and soon we walked out of our cottage. My hardon was pointing the way to the beach. While my brain was still half asleep, my dick was fully awake and anticipating being buried in my sister’s pussy.

While my cock wanted to go to the sunbed, my sister had a different idea. She pulled me by the hand and started heading off to the left, past the cottages. I asked her where we were going, and she smiled and told me to be patient. We walked for a few minutes. I had a sneaking suspicion about where we were headed.

“Good morning.” It was a male’s voice as we walked around the patch of bushes. It was Robert and his wife and daughter who were with him.

“We were hoping that you two would join us this morning. I’m Wendy and this is my daughter, Becky.” Both gave me a little way.

I wave back. “I’m Josh.”

“Last night Kelly said that she might want to try yoga today.” It was Robert.

I’ll admit to being a tad bit jealous when I saw how he looked at my sister. Kelly got a big grin on her face as she looked at the huge dick hanging between Robert’s legs.

“We brought a couple of beach towels if you’re interested Josh.” Wendy smiled at me.

As I mentioned earlier, mother and daughter look alike. Both looked to be about five foot six and were thin. Both had what looked to be B cups that sat up high on their chests. Both had medium sized nipples which topped half dollar sized areolas. Wendy’s most striking features were her well defined stomach muscles and her muscular arms. They didn’t look steroid enhanced, rather a mark of someone who worked out a lot.

My sister wasted no time grabbing a towel and standing next to Robert. She bent over at the waist as she spread out the beach towel, giving him a good look at her pussy and asshole. Wendy and Becky smiled while we all watched Kelly flash. Me, I just bend down onto one knee as I spread out my towel. Becky moved her mat so she could be with me and her mother.

Wendy turned out to be a yoga instructor, so she told us the moves to do. The first was just touching our toes. I bent down and touched my toes and held it for fifteen seconds. When I stood back up, Wendy said that I needed to go slower and to breathe in as I was standing back up. The next pose had me standing with my feet should 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.

Wobbling a little bit as I tried to hold the poses and breathe in and out slowly, it was embarrassing when my legs shook. Becky smiled at me and said that it’s harder than it looks. I smiled back, noticing that she had a tiny birthmark just above the crease on her left thigh. I noticed when I was looking at her bald pussy. She looked to be about my age, fifteen or sixteen years old.

Wendy took us through the through several more moves. At one point, she walked over as I was trying to strike a pose that had me on one knee and the opposite hand. My other hand and leg extended behind me. My cock started to twitch when Wendy come up behind me, grabbing both of my hips while trying to steady me. I looked over towards my sister and saw that Robert was behind her too, helping to stabilize her. The difference being that Robert was not behind Kelly, but in front of her. His giant cock was less than a foot from my sister’s face. We held the pose for almost thirty seconds and then got down on our hands and knees.

The next pose was the one we saw the family doing the day before. Kelly had called it the downward facing dog. At Wendy’s direction, I planted me feet and hands on the ground and raised my hips as high as I could get them. I watched as Kelly did the same along with Becky.

Robert came up behind Kelly and I thought he was going to help her hold the pose. He grabbed her right hip and then I saw him slowly push his finger into Kelly’s pussy. He pulled it out and then plunged a second finger into my sister.

Focused on Kelly, I didn’t notice that Wendy had straddled my shoulder and grabbed my hips to pull me up higher to the sky. What got my attention was a pair of hands spreading my ass cheeks apart and a wet tongue along the skin between my ball sack and my asshole. Becky’s hand wrapped around my cock which started to swell. The broad part of her tongue licked up and down between what would be the bottom of my ball sack and my asshole. I felt my ass being spread wider and that’s when I felt the pointy tip of a tongue on my asshole.

“Holy Fuck.” It surprised me, disturbed me and made me hard as hell and that’s why I called out.

“Are you okay Josh. We’re teaching Becky how to rim guys. I hope you don’t mind if she practices on you.” Wendy said it like she was talking about teaching her daughter how to play the piano.

“Yeah.” It was all I could say as the I was getting my ass rimmed by a young woman.

Wendy held me up as my arms and legs started to grow tired from holding the pose. I didn’t want to stop, I was starting to like the feeling of Becky’s tongue playing with my ass. At one point, Wendy let go of one of my hips and pressed a finger against my butthole. In a flash my mind feared that she’d slide a finger into me and that’s just what she did. I should have been horrified at what happened, instead I moaned. Becky continued to lick my balls as her mom slowly pushed a finger in and out of my asshole.

It was Robert’s voice that caused Wendy to pull her finger out of me and for me to look over at Kelly. My sister was kneeling before Roberts as she sucked his gigantic cock. The thing had to be close to a foot long and the girth close to a soda can. Robert had suggested we move to their cottage. With Becky standing up and walking next to me, I fell to my knees and then slowly stood up. I got up and followed my sister and Robert, walking the roughly fifty yards over to their cottage and sunbed.

It didn’t take too long before my sister and Robert were in a sixty-nine position. Wendy spread her legs, giving me the come-hither motion with her finger. I knew what she wanted, and I was happy to oblige. She tasted sweet. My tongue found her swollen clit as I pushed my index finger into her pussy. It took a few seconds to find, but her swollen G-spot was right where I expected to find it. Wendy moaned and grabbed my head.

With my mind focused on pleasing Wendy, I didn’t give much thought to what Becky was doing. I just expected that she’d either join her father or plant her pussy on her mom’s face. She didn’t do either of those, she went back to licking my asshole and stroking my cock.

“FUCK! FUCK ME!”. It was my sister and she screamed loudly. She had most, but not all of Robert’s cock buried in her pussy. I pulled my face out of Wendy’s pussy long enough to look over at my sister taking what is likely the biggest cock she’s ever had.

Returning to Wendy’s pussy, I licked her clit and fingered her G-spot until she had a back arching orgasm. Not letting up my tongue assault, I was treated to the taste of sweet pussy cream spraying into my mouth and onto my chin. I used my tongue to scoop up the milky fluid, downing it as quickly as I could get more into my mouth.

Wendy pulled my face from my pussy which allowed me to focus on the tongue licking my asshole and the hand stroking my rock-hard cock. Becky pulled her tongue away from my rear and let go of my cock at her mother’s direction. We played musical chairs and soon Becky was on her back, and I had my shaft buried in her tight, wet hole. As we were switching positions, I looked over to see Kelly getting rammed doggy style. Her eyes were closed, and she was whimpering as Robert’s massive cock continued its assault on her pussy.

“Fuck my daughter, Josh. Let me watch you thrust in and out of her pussy.” Wendy climbed up on the sunbed and was soon straddling Becky’s face.

Thrusting into Becky, I watched her mother feed her the same creamy pussy juice that I’d tasted earlier. Becky was tight, but not as tight as Sam. For a fleeting moment I wondered how often she is fucked by her father’s huge cock.

Thrusting deeper into Becky, I grabbed her hips and lifted her ass up a little to meet my thrusts. Wendy talked to me as I fucked her daughter. She kept telling me to fuck her daughter’s ‘tight little cunt’. Don’t get me wrong, I love talking during sex, but this was a little excessive. Thank the lord for my sister’s blood curdling scream from her latest orgasm. Between Kelly screaming and the ministrations of Becky’s tongue, Wendy stopped talking and ground her pussy into her daughter’s face so she could orgasm.

When she finally caught her breadth again, Wendy spoke. “tell me when you’re getting close Josh. I want you to cum in Becky.”

I kept thrusting into Becky, giving her a moment of rest as each orgasm rocked her body and then returning to burying my cock in her. With each thrust I was getting closer and closer. Feeling the seed inside me almost reaching a boiling point, I told Wendy that I was getting close. The older woman climbed off her daughter’s face and got off the sunbed.

Focused on reaching the end, the world around me closed in so it was just my cock and Becky’s pussy. I was going faster and faster, each thrust bringing me closer to orgasm. I was just about to unleash a torrent of seed when a slimy finger wiggled into my butthole. My shock momentarily caused me to stop thrusting. Wendy pushed my hips with her free hand. I pushed in at the same time as the finger inside my ass found a swollen spot and I erupted into Becky’s pussy.

Wave after wave of seed pumped into the young woman under me. It was by far the most powerful orgasm I’d had in my life. The seed just kept coming out. I must have thrust into Becky thirteen or fourteen times. With each thrust, it felt like more and more seed was draining from my nuts. When I stopped thrusting, Wendy removed her finger from my asshole. I looked over at the other part of the sunbed to see my sister and Robert watching me.

Wendy kissed the side of my face. “I take it that’s the first time you’ve had a prostate massage as you’re orgasming. I hope you liked it.”

I was at a loss for words. I’d just fucked a young woman after she rimmed me. Add onto that, her mother fingered my asshole as I was cumming in her daughter’s pussy. I rolled off Becky and watched as her mother crawled between her legs. We listened to Becky moan as her mother licked and sucked my cum out of her daughter.

The sun was fully above the horizon now. Once she was finished eating my cum out of her daughter, Wendy crawled up my body and gave me a kiss. I could taste pussy and what was surely my own cum on her lips. Wendy then kissed her daughter and husband. My sister blushed at Wendy’s question about riding her husband’s dick. Kelly mentioned that it’s biggest dick she’s ever fucked. The smile on my sister’s face went from ear to ear when Wendy said that she could fuck her husband anytime she wants.

We talked for about fifteen more minutes before Kelly mentioned that we needed to get going and that our parents were probably looking for us. Robert invited us both back for another morning yoga session tomorrow if we wanted to join them. My sister grabbed my hand and pulled me off the bed, but not before giving Robert a passionate kiss and small kiss on the head of his now half hard dick.

“Let’s head back to the cottage and see if mom and dad are awake.” Kelly gripped my hand as we started walking back to our cottage.

“Did you enjoy fucking Robert?”

“Oh my God! His dick is huge, and it felt like he was splitting me in half with it. I swear it felt like he was filling my entire womb.”

“I don’t think I’ve ever heard you scream so loud.”

“That is by far the biggest dick I’ve ever fucked. He has Jamal beat easily.”

“Jamal. You fucked Jamal from the basketball team? I heard that he has the biggest dick in school.”

“Yeah, I fucked Jamal and no, he doesn’t have the biggest dick in school. That title belongs to Mr. Evans, the science teacher.” My sister shot me an evil grin. “Don’t look surprised. How do you think I got a ‘C’ in chemistry? I didn’t fuck him, but I did suck him off. Mr. Evan’s dick is longer than Robert’s. There was no way I was letting Mr. Evans destroy my pussy.”

‘Holy shit Kelly, you had sex with a teacher.”

“I came onto him, it wasn’t like he hit on me. I needed a better grade, and he needed a pair of lips around his huge cock. It worked out and I got to graduate.”

I looked at my sister. “How many times did you suck him off?”

My sister thought for a moment. “I think three or four times. It was close to the end of the school year. So, there were lots of girls around school looking for help and extra credit if you know what I mean.”

“Wow.” It was all I could say.

“You ought to try it Josh when we get home. Having sex with adults is fun. I let one of the substitute teachers fuck me when I was sixteen. I was going through my ‘dad crush’ phase. I looked like his stepdaughter, and we just clicked one day.”

“I think I had my share of adult women back there.”

“I know, I saw Becky rimming your ass. That was hot. How did it feel?”

“It’s weird. It felt disgusting and strangely pleasurable at the same time. I can’t believe she shoved her finger up my ass just before I was about to cum in Becky.”

“That was fucking hot. You should have seen the look on your face the moment she pushed her finger into your ass and then a second later you blew your load.”

“It was weird. I just kept cumming and cumming.”

“I could tell.” My sister squeezed my hand as we walked. “Maybe I should try that with you.”

“FUCK NO. Keep your fingers away from me.”

“Are you sure Josh. If I keep my fingers away from you then I can’t stroke your cock.” Kelly poked me in the ribs with her free hand.

I thought about it for a moment. “Okay, you can touch me with your fingers. Just keep your fingers out of my asshole.”

Kelly looked at me for a few seconds. “Fine Josh. Whatever you say.”

We walked for a few more minutes and eventually made it to our cottage. We walked in and found it empty. Kelly and I looked at each other and then she said something about mom and dad probably going to the restaurant for breakfast.

I needed to brush my teeth, so I excused myself and went to the bathroom. While looking in the mirror as I scrubbed my pearly whites, I realized that I needed to shave off the weeks growth from my face. I don’t have a lot of facial hair, so I was able to lather my face and save in about two minutes. When I emerged from the bathroom, my sister was sitting on the sofa waiting.

Kelly stood up and walked over to where I was standing. Running her hand across my face and then across my balls, she commented on how smooth both were. Grabbing my hand once more, my sister pulled me out the front door and towards the restaurant. We walked by the pool and two people lounging by it, Elsa and Freya. Both waived as we walked by but continued their conversation.

We found our parents along with Sam and her family. My mother had a big smile on her face as we walked into the restaurant. My sister and I grabbed food and then pulled up an extra chair at the table our families were occupying. I was halfway done with my second pancake when my mom spoke up.

“You two got up early this morning.”

“Yeah mom, Josh and I wanted to take a walk.” Kelly put her fork down and took a drink from her glass.

“Did you do anything fun?”

“Just some yoga.”

“Yoga. I didn’t realize that you two did yoga. When did that start?”

“The first time was today.” Kelly took another bite of her eggs.

“So did you do this on your own or did someone help you?”

“Someone helped. It’s no big deal. They were happy to have us join them.”

“Someone helped you.” My mother paused for a moment. “Would that someone happen to be the dad you were talking to in the bar last night? You know, the guy with the huge dick hanging halfway down his thigh.”

“It might have been him.”

“So did you have ‘fun’ doing yoga?”

“Yeah mom, I did have ‘fun’. I think you should ask Josh how much ‘fun’ he had.”

I shot my sister an evil stare.

“Sweetheart, did you have fun at yoga?” My mother looked at me.

“Yeah, it was okay.” I didn’t hesitate in my answer. I hoped by being quick and saying more than ‘yeah’, my mom would stop interrogating us.

“Okay. Josh, I saw that mom and her daughter, and they are more than attractive. It had to be better than ‘okay.”

‘Mom, ask Josh what happened when he was eating Wendy’s pussy.”

I shot my sister another glare, this time the laser beams coming out of my eyes could kill an enemy starship. Now everyone was looking at me.

“Well Josh. What happened?” My mother folded her arms across her naked breasts.

“Nothing.”

“You say nothing happened and your sister says that something happened. Which is it?”

“It’s nothing mom.”

My sister spoke up. “Josh got rimmed by their daughter when he was in the downward dog pose. Wendy is a yoga instructor and she held Josh’s hips up while her daughter rimmed his ass.”

The look on everyone’s faces said it all. I could tell my mother was about to say something and then thought better of it.

“Does anyone want some more juice.” It was Sam that spoke and broke the silence. “Come and help me grab a few more classes of juice.” Sam grabbed my hand and pulled me up.

“Sorry your sister was a bitch back there.”

“It’s okay.” It wasn’t but I didn’t want to tell Sam that. I was feeling a small amount of shame, since I didn’t want to admit that kind of liked it when Becky rimmed my ass. I definitely didn’t want to admit how strange and good it felt to have Wendy rub my prostate as I was cumming in her daughter.

With a few glasses of juice in hand, we returned to the table and found the conversation had moved on form the sex session my sister and I had the hour before. The families were planning to go snorkeling and were discussing the time that the dive shop opened. In the end, our families agreed that going at ten in the morning would give us a few hours of time in the water before grabbing lunch.

We talked for another thirty minutes before heading back to our cottage. On the way out of the main resort building, the moms stopped by the front desk to ask about the afternoon activity planned. The front desk said that today is another volleyball tournament. After discussing it with the group, we all decided that we’d skip playing in the tournament. The twins and my dad said it would be fun to watch however. My dad gave me a sly smile. While I didn’t smile like him, I knew he wanted to look at bouncing boobies playing volleyball.

Heading back to the beach, my mother grabbed my hand and walked with me.

“Don’t be mad at your sister for telling us what happened earlier this morning.”

“Why can’t I be mad?”

“This trip is supposed to be about growing up and trying new things Josh. If you don’t explore, then you’ll never know what you like and don’t like.”

I thought for a moment. “I’m okay with exploring, but Kelly didn’t have to tell everyone.”

“Did you fuck Wendy and her daughter in their cottage?”

“No.”

“You do realize that anyone on the island could have walked by and seen you sweetheart. How do you know that I didn’t follow you and your sister to watch the two of you fucking. I could have seen everything.”

“Yeah, that’s true but now everyone knows what happen.” I pondered for a second. “Did you mom?”

“Did I what sweetheart.”

“Did you follow Kelly and I to watch us fuck?”

My mom turned her head and smiled at me. “No Josh, I didn’t follow you and your sister.”

We passed the pool and continued following our families as they headed back to the cottage. “Can I ask you a question Josh?”

“Sure mom.”

“Did you enjoy it?”

“Enjoy what?””

“Did you enjoy it when Becky rimmed your ass?”

I didn’t say a word. Conflict swirled in my brain. If I admitted to liking what Becky did, then my mom could get the idea of doing that to me. If I lied and said no, then I’d potentially miss my mom licking my butthole. We kept walking as my brain worked out what to say.

My mother tugged on my hand and made us stop. “I know you are thinking of how best to answer my question. This is the time in your life when you’re supposed to be discovering what you find pleasurable. It’s the reason we brought you and your sister here. How about I ask you the question again after we’ve left the island?”

“Sure Mom.”

My mom leaned in and kissed me. Wrapping me in her loving embrace, my chest melded into her big tits. A tongue slithered it’s way past my lips and into my mouth. A hand grabbed my ass and held it. We kissed for several seconds and then it ended. My mother released me but not before squeezing my ass cheek.

“I’m hoping you say yes. You have a cute ass Josh.” With that my mother grabbed my hand and we started walking again.

As we walked, I wondered if my mother really wanted to rim my ass. A strange idea popped into my head. Was my mother jealous that she didn’t rim my ass first? She seemed overly focused on who took my virginity. I started to wonder if this was like that. She wanted to be the first at something with me and she wasn’t.

By the time we reached the cottage, we found my dad and sister talking in Spanish with Maria, the housekeeper. I caught most of the conversation, which was mostly about Maria. She was talking with my sister about her family and how long she’s worked for the resort. Maria looked at my dad’s swelling cock and smiled. She kept looking at my sister and then at my dad and back to my sister.

My mom whispered in my ear that we should head out to the beach to meet our neighbors. Grabbing my hand, my mom pulled me away from my dad and sister who were continuing to flirt with the housekeeper. Walking out to the beach, we found Sam’s dad slowly fingering his daughter as he applied sunscreen to her back.

I grabbed the bottle of sunscreen and applied it to my mom’s backside. Once mom rolled over, I applied more sunscreen and took the opportunity to play with her nipples. I rolled them between my thumb and forefinger until they were hard. Switching places with my mom, she applied sunscreen to my body. I was wondering if she would finger my ass given our earlier conversation. The hands across my ass stopped at my butthole but didn’t linger too long. After a few minutes my mom declared me protected and sent me off to play with Sam and her brothers.