Part 1

Nothing exciting ever happens in this town. I know I know. This is what every 16 year old boy complains about, but seriously it’s the same routine, day in and day out. Go to high school: walk home with my sister; mom and dad come home from work later; eat dinner; jerk off; go to bed. Rinse and repeat. Don’t get me wrong, I love my family, even my stuck up sister, but I need more.

So leading up to summer I made sure to drop hints to my parents that we needed to do something grand. My mom and dad are never ones to shy away from a challenge, and dutifully set out to shut me up. A little before school was to let out they called a family meeting (yes, those don't just happen on TV) and announced they’d booked a vacation to a luxury resort in Jamaica.

I couldn’t stop myself from exclaiming, “Holy shit!”

“Language, Jason,” my dad said with a smile.

“Yea, relax dork,” my sister chimes in. “ Don’t act like you’ve never been anywhere before. You'll sound like a yokel.”

“Be nice to your brother, Lily. He’s just excited. We know how you guys have worked hard this year and deserve a good time.”

“Yea, be good you two. Your mom and I talked about how we want to start trusting you, and this vacation is part of that. We plan to give you guys a little more freedom there, so you have to look out for each other. From what I hear, they are pretty relaxed on their drinking age, but step out of line and you’ll be stuck with mom and dad and virgin Shirley Temples the rest of the trip.”

“Virgin drinks for a virgin boy,” my sister sniped.

“Screw you, Lily. You’re just sour since you’re not getting it on the regular since Derek broke up with you?” I regretted it as soon as I said it, but she’s been a real bitch since she walked in on Derek going to town on a mutual friend at school.

My dad let out a sigh of exasperation. Or was it something else?

My mom chimed in, “Both of you stop. Lily, drive your brother to the mall and pick out some vacation clothes. We’ll be beachside for much of the vacation but we might do some hiking too. Get along.”

———————-

On the drive over to the mall I felt a little bad about what I said to Lily in the heat of it. Truth is, we are usually pretty close. Mom shot us out in quick succession so Lily is only about a year and a half older than me. The family joke is that my dad waited the exact amount of time the doctor recommended before pouncing on mom again after she had Lily, and poof, here I am.

“Sorry for being a jerk,” I murmured.

“Sorry for the virgin jokes.”

After an awkward silence, she asked, “What’s the deal with that by the way? Shouldn’t you be living it up and knee deep in girls. What’s the hold up?”

“I don’t know. It just never works out.” And that’s the truth. I’m confident enough to say, I’m a pretty good looking guy. I’m 5’11”, with black hair, hazel eyes, and I’ve been told, a nice ass. I keep in shape, and am quite proud to show off my 8 inch cock where I can. What I couldn’t tell my sis was that I’d been close so many times. Something just gets in the way. With my last girlfriend, we did everything. Handjobs, blowjobs. Hell, even titjobs (she had massive tits. It was fantastic). And don’t think I didn’t give back. I eat a pussy like no other. I actually really love going down on girls. Having someone clamp down on your head with their thighs while you circle their clit with your tongue and the explode in rapture is incredible.

But as soon as it got time for the main event, her family upped and moved because the mom's job transferred her out of state. Jerking off together over video chat loses its allure pretty quick when you’ve almost had it all. And various hooks ups after that just haven’t got there.

It’s been so long since I’ve had any real sexual contact that I’ve developed a pretty involved cam2cam habit on Omegle. It’s kind of fun to jerk off with some random girl. And to discover the thrill of having gay guys beg to see your dick and watch you cum was a nice bonus too. Like I said, I’m not shy about showing off my dick. But this vacation needs to go well. I have to fuck someone. Maybe I’ll find some hot island teen who will let me fuck her on the beach. Just the thought was making me hard when my sister's voice brought be back to reality.

“Well, maybe in Jamaica I could be your wingman. I’ll help you pop that cherry.”

“Thanks...” It was kind of weird to see her be THIS chummy with me. Must have made her feel really guilty before. Hearing her talk like that made my cock stir even more. She wasn’t helping my frustration in the least.

At the mall we hit up the regular spots for some clothes and decent hiking shoes. We headed to the bathing suit section and went to try a few things on. I chose some run of the mill board shorts and with my sisters encouragement for some more stylish short trunks that hugged my ass and junk. All the rage with the ladies now, she assured me.

What I wasn’t prepared for though, was how incredible my sister looked in a bikini. It’s been years since we went to the beach together, and sure around the house I’d see her in all manner of dress (and undress between showers- we can be pretty liberal in our house). But nothing compared to seeing her in a black suit, tied with a tiny string in the back and hugging her body. She was about 5’3”, very fit from years of soccer, perfect C cup tits, and an ass that put her squarely in the category of PAWG. The suit wasn’t a thong up her ass by any means, but there was just plenty of skin to see. For years, I have tried to resist the urge to stare at her ass while she ran up and down the field in soccer. Not to gild the Lily here (pun intended) but her body has even caught dad's eye on occasion. He'd never admit it, but I think he sometimes enjoys a peak at his beautiful creation. Seeing her like this also made me appreciate how sexy her red hair was when against her pale skin.

“Jesus!” I really couldn’t keep my mouth shut. I had to work on that.

“What?” Lily seemed surprised. “It’s a one piece. It’s no big deal.”

What she called one piece was technically true, but there were plenty of slits and cleverly placed open spots that left less to the imagination than any of Aunt Amy’s one piece suits.

“Well glad you like it, perv. I got a few more that put this to shame. It’s Jamaica after all. I assume the competition for attention on the beach is going to be fierce. I need some love too!” It was good to see my sister less stuck up, and back to her old attitude. Needless to say, that night I logged on to the camsite as soon as I could.

—————————

The flight to Kingston, Jamaica was over 5 hours. Just long enough to take a nap and still wake up restless. Lily was back to her stuck up self and kept her head in her iPad most of the flight. Mom and dad sat separate from us and were extra cuddly in their business class seats. Vacation always brought out a lightness in them which was nice to see. I nudged Lily at some point to gesture over to what I assume was mom's hand at dad's crotch under the blanket. You couldn't tell from their faces, but I swear mom was expertly jerking dad off without being seen. Could have been my imagination though.

"Gross," Lily said quietly, but I could detect a hint of a smile on her face as she shifted in her seat. She enjoyed our parent's closeness as much as I did. We had relatively young parents. They were high school sweethearts and had Lily at 18 as a "happy mistake." My mom was 36 and I'm proud of how my friends talk about her as a "MILF." My sister and I must have got our athleticism from dad, because mom's body was more lithe and slender. She had the same pale skin and red hair as my sister, with at most B cup tits that still stand up firm and perky. Her ass was full and round, filling out her mom jeans nicely. She keeps in shape with periodic bouts of yoga like most suburban moms, which is enough to keep herself nearly as flexible as she was in her teen gymnastic days. Dad is 36 as well and has the kind of body you can tell used to be all muscle but is on its way to being a "dad bod." He's about 6'0", with black hair like mine, and a hairy chest. Together, they make a good looking pair.

The plane landed and we took a shuttle for what seemed like a good while to the resort, which was apparently on a beach set apart from the main touristy spots.

"Where is this place?" As I said this, I noticed that there was only one other set of people on the shuttle; a dad and his daughter.

"Told you kids, we spared no expense," my dad said. "This place is supposed to be pretty exclusive. A friend from work recommended it to me. Said he takes his kids here all the time. Honestly, I just looked at the 5 star reviews and trusted my friend." I could tell he was beginning to get a little nervous. Dad likes to take ownership and credit for our vacations, so it means that it's on him if it doesn't go well.

Pretty soon the road opened up and before us was a beautiful, modern looking resort, set among a background of shining blue water. Some of the worry started to melt away. If it's this gorgeous, what could go wrong? Lily, mom, and dad were all entranced with the water, but something else had caught my eye. It flashed by so quick that I could question what I saw, but I swear I just saw a naked man and woman walking to the resort on the side of the road. They must have been wearing bathing suites and I just couldn't tell.

The shuttle pulled up to the palatial entrance, and two porters rushed to take our bags and welcome us in. We walked in to the lobby to the front desk, eager to get to our rooms.

"Wait until you see the rooms your dad and I picked out. Two nice big adjoining suites. You and your brother will have your own suite as part of the independence we want to encourage. But your dad and I will of course have a key." That sounded awesome, especially if I was going to bring back an island babe to the room. Though I was beginning to get the impression mom and dad wanted the space for themselves too.

"Honey....?" I heard my mom say in a worried tone. I looked over to see her staring at the couple I had seen on the road earlier. Sure enough, they were stark naked! They were a black couple, tall and attractive. The girl had very dark skin, and melon sized breasts with the most perfect small dark nipples to top them off. The guy was bald, with a beard and sunglasses, a six pack and the biggest dick I'd ever seen. And from the looks of if, the biggest one Lily or my mom had seen. While mom’s face was of shock, Lily looked like she was trying to soak it all in. The guy apparently noticed and shot a smile to my sister that made her blush.

I looked over to dad to see his reaction, but he was busy arguing with the concierge. As much as I didn't want to tear myself away from the image I would most likely be masterbating to later, I went over to see what was wrong.

"But I've got kids with me. I listed their ages when I registered," I heard my dad say.

"Yes, I see here, 16 and 17. That is not a problem sir. We allow any family to stay here, with only some restrictions on areas and activities for 16 and older. It is all here in the pamphlet. Now, please let Amelia show you your rooms as I have others guests to register." By that he meant the father and daughter who were on the shuttle and seemed eager to get to their rooms. The dad was holding her up on his back by her legs, giving me a nice view of her little ass as she wiggled excitedly. It didnt seem like their first time here.

"Family meeting!"my dad called, as he signaled for Amelia to wait. She shrugged and stepped back to give us some space.

"What did they say, honey? And did you see that naked couple. I mean his..." My mom stoped and shot my sister and I a look.

"I dont know how to say this, but apparently this is a clothing optional resort. Like I said, its well rated, but the norm here is to be nude in most of the areas, except the formal dining room. I'm so sorry kids, I think we might have to leave."

Surprisingly, my mom stopped him." Wait a second. We've come all this way, and I'm sure we wont get our deposit back. Lily is almost 18, and Jason is a very responsible young man. Plus, you and I have always talked about going some place like this." Lily’s eyes worriedly shot back and forth between us and the black mans dick. It’s as if she was worried it would disappear.

"Alone! Not with the family. Back me up here kids."

"Relax dad," Lily said. "Its optional right? Meaning if someone chose to they could keep their clothes on. I bet only gross old men will be letting it all hang out. And Jason sees plenty of tits on his cam sites, so its no big deal to him."

"Hey!" I shouted. She wasnt wrong about how much porn I've seen (though how did she know I visited cam sites), but it was very much still a big deal for my 16 year old mind to see glorious naked bodies. As they were arguing I was already building elaborate fantasies of what could happen here.

My mom spoke up again. "Honey, I really think we should give it a shot. We did say we wanted to give the kids more leeway and responsibility. Well, here is their chance for them to show us they can handle some adult fun."

I could tell my dad was not completely sold, but he always trusted my mom and often relented to her. She's always been more go with the flow. Thank god for that right now!

"Ahem," Amelia finally spoke. "Please, we must be on our way. Let me show you to your rooms. I am sure you are eager to get out of your travel clothes and begin enjoying the resort."

"Fine," my dad said. "Thank you. Please show us to the rooms."

"Right this way."

Hell yes, I thought to myself. All I had to do was get away from my sister, and a whole resort of pleasure was up for grabs. I could tell my horny mind was getting carried away, but I didn't care. As we were shown to our rooms, I saw the father and daughter from the shuttle making their way to their rooms as well. I guess it was no crazy surprise for them what this place was all about. They seemed especially comfortable, as the dad walked with his hand in the back pocket of her tiny jean shorts.

"Huh, close family" I thought.


Part 2 to come soon

 

Looking forward to part 2

 

Great start, love the story, cant wait for part 2.

 

Yeah definitely need part 2, 3, 4 and how ever more it's goin to take to tell the whole story.. starting off great

 

Part 2

We followed Amelia to our room, and with each nude guest we saw I could see my dad turning bright red. He seemed to be the only one, as mom was chatting energetically with Amelia about the amenities and activities, and Lily was meeting each guest with a smile.

"If I didn't know any better, I'd guess you were excited about this little mix up," I whispered to her.

"As if you aren't. I saw you sporting a half chub staring at that guy and girl in the lobby. What do you say, should be find them so you can finally fuck?" She was teasing about my virginity again but this time it felt different. She wasn't angry...it was more playful. Even flirty. I decided to play right along.

"Let's do that," I joked back. "And you can come along since you couldn't take your eyes off that huge dick. You think you can take that whole thing?" I was internally cringing that I was going too far. But as I said it, a look of hope or eagerness quickly passed over Lily's face.

"Did you hear that kids," my mom shouted back to us,"They have plenty to do. There's even an art class you can take where you can do some live figure drawing. Maybe that will be a nice ice breaker before we all brave the beach. So many bodies right away might overwhelm you two!" My mom is incredible. She is really trying to just go with it and not lose her mind.

"Sure mom." I shrugged at Lily whose expression assured me that taking a class on vacation was the last thing she wanted to do. "Come on," I assured her. "Let's just do that class to give mom and dad time to figure stuff out." And to continue our flirty game, I added, "There will be plenty of time for you to ogle all the cock you want." Phew, I got a smile from her. Shit, was I flirting back? If she wasn't my sister, you'd think I was trying to fuck her. Come to think of it, if she wasn't my sister, I would be trying to fuck her. There have been plenty of times I heard her and Derek fucking in the room next to mine, and I'd be lying if I said I didn't jerk myself to sleep hearing that.

“Here we are,” Amelia said, stopping at the end of a hallway with two adjacent huge doors. To the right are the parents, and to the left the young ones.” She used her key to enter the room on the right and ushered us all in.

The heaviness in dad’s shoulders seemed to drop immediately as he took in the room. “Well at least there is this!” He was right. The room was huge and split into two. There was a kitchen area that looked over a decent sized lounge with a giant tv, comfortable couches, and a full wall of windows that looked over the beach area. Through a door brought you into the bedroom that held a king sized bed, in-room hot tub, and a bathroom suite with a giant glass shower with marble bench seating on one side. The glass of the shower went all the way to the ceiling, and Amelia informed us that it could be used as a steam room as well. Back in the bedroom, Amelia opened a door that connected to the lounge area of my and Lily’s room.

“As requested, the rooms are identical, save for the two queen beds rather than the king bed.” At a knock at the door, Amelia said “Ah, here is your luggage,” ushering in a young male porter. “If there is nothing else, I will give you some privacy. Please do not hesitate to call the front desk for any of your needs, no matter how personal. We do try to make your stays as comfortable and pleasurable as we can. Also for a list of activities and resort map, you can press the “information” button on the tv remote. And with that, she handed us the keys with an extra set so we could get into each other’s rooms, and left

“What do you think kids!” Dad was excited again. He was hoping the rooms would make up for his lack of research into the hotel.

“It’s wonderful, honey,” my mom said, stroking his arm. Always the supporter.

“It’s amazing dad. Good work. Hey, check out the view. I think I can make out some naked folk running around on the beach from here!” Lily loved to tease dad. They were definitely closer, and I was closer to mom. While Lily’s teasing was meant to be lighthearted, it brought all the redness and worry back to dad’s face.

“Oh, sweetie. I’m so sorry. I...I didn’t know...”

“It’s fine honey!” Mom to the rescue. “I’m going to take your father to the room to unpack and settle him down a bit. Why don’t you kids get comfortable and look for that class. We’ll meet back together for dinner.” And with that she pushed my father through the joining door and locked it.

“Nice one, sis,” I said as I immediately cracked open a beer from the mini fridge.

“Already?” She said looking at my beer.

“Hey, it’s all inclusive and it’s vacation. You take one too and loosen up. I want my nice sister, not my stuck up one.”

She caught the beer I threw her. “I’ll have to make it a shower beer. Your nice sister doesn’t smell nice ...shit the class thing is in an hour. Not enough time for us both to shower and get ready. Tub time then?”

Tub time is what we called it as kids when we would bath together because our parents were too exhausted to give us individual baths.

“Aren’t we a little old for tub time?”

“Shut up and just put on your board shorts, then meet me in the shower. Bring your beer.”

Something about her the way she was ordering me around I enjoyed in that moment. “Alright weirdo. We’re missing the rubber duckies though.”

Lily disappeared into the bathroom with her bathing suit in hand, while I rummaged through my stuff to find my suit. I heard her turn the shower on and took that as my cue to enter.

“Ah, what the fuck Jason!”

Apparently I came in too soon and as a reward was treated with a gorgeous view. My sister was standing there in one of her bikinis but had not had a chance to get her top on yet. Her hair was tied up in a scraggly, red mass and obscured nothing of her upper body. Her breasts were so pale and perfectly sized. Not a hint of sag, and her nipples stood out as tiny and pink on nickel sized areolas. The steam building up in the shower behind her made it all feel like a dream. I felt like I stood there for an hour at least, taking in everything I could before I could stammer out, "ssssorry!" I turned to the wall so she could finish.

"Ugh, its fine, turn around. You've already seen them and if we are going to be staying at this resort, you should probably get used to not reacting to every pair of tits you see."

"Are you sure?"

"Don't be so timid, dork."

And with that I turned around to get my second view, almost as good as the first. Nothing beats the first.

"Like I said, you have to get that under control if we are going to be walking around together. You won't be able to get a girl if you are constantly sporting a hard on."

I blushed. I hadn't even realized the effect she had had on me. Sure enough, my dick was straining against the edges of my suit, giving a nice outline of my manhood, circumsised head and all. I tried to play it off as a joke. "Hey, I'm topless, your'e topless. Only fair right?"

"Ha ha perv," she said, not taking her eyes off my bulge. "Let's hurry up and shower and get dressed to go. Mom will be annoyed if we don't take her suggestion and get to the art class."

We entered the shower, which had ample space, and soaped up our bodies. I couldn't help stare as she soaped up her tits, making little effort to turn her body away. Watching her lather her thick ass almost made me bust my load right then and there. I'm pretty sure I barely washed up, instead choosing to tortured myself with views of her body.

As we dried off, Lily suddenly turned to me with a devilish look in her eyes. "You got your eyeful and I'll get mine. You owe me, perv." Again we were playing some game, but I didn't know the rules. I just knew enough not to cross her.

"Fine, I owe you, whatever." I was beginning to enjoy when she called me a perv.

______
On our way to the class, we passed by our parents bedroom, and I could have sworn I heard muffled moaning, but I didn't have time to check it out.

In the class, there were 8 easels set up in a circle around a stage. Lily, now dressed in her bikini, and I, in my suit and with no shirt, sat down beside each other in the last two available easels. I took a look around and to my embarrassment Lily and I were the only two people wearing clothes, including the resort's indoor activities coordinator. He was a man in his 50's, maybe Puerto Rican, medium height, slender body and an uncircumcised penis hanging between his legs. His face seemed kind and serene.

"Welcome everyone. I'm Paul and as a break from the beach going and partying, its nice to sometimes sit still and put our hands to creative use. Everyone help yourselves to some drinks and we will begin once the model arrives.

"Bottoms up," I cheers with Lily and drank the provided chilled wine in one gulp.

"Uncultured slob," Lily jokingly sneered, but knocked hers back just as quickly. Looking around the room, we were definitely the youngest, and it was a mix of men and women. Two girls caught my eyes as they seemed to be a couple. As they drank they stayed close, and one gently circled the others lower back with her finger. Such as small move, but while naked, so erotic. (Yes, I'm a horny kid perving on a nice lesbian couple).

"Well, it appears we may have to postpone," Paul announced. "Our model isn't coming. Unless we can get a volunteer."

I looked over at Lily expecting disappointment, but was met with the same devilish eyes from the room earlier. "Remember, you owe me" is all she said before announcing "My boyfriend would be happy to chip in" while raising my arm in the air.

Before I could say "Boyfriend!?" the rest of the class gave appreciative claps, and Paula came my way.

"Come come, let's hurry. Thank you so much. If you would please disrobe and take a set on the stage before I direct you in your pose."

Before I could protest, Lily had undone my suit's tie and "helped" me out of my shorts. I said "helped" because she really just pantsed me. I think she was enjoying the prank a bit too much, because she didn't think through what would greet her while bending down to pull off my pants. No sooner had she got them off than she had come face to face with my semi hard (but confused) penis. A look of shock registered, before an expression of quick desire.

Paul pulled me onto the stage, and posed me. "Lean this way please, and move your leg like so," Paula directed, not being shy to grab any part he pleased and move it where he wanted. I was posed with one arm resting atop my head, the other to the side, while leaning half an ass cheek on the chair. Totally exposed. "In the next 30 minutes I want you all to try to capture this young man's vigor and strength." Paul turned to whisper in my ear, "I need you to show some more strength, please." As I clearly did not understand him, he sighed, said something about "tricks of the trade" and surreptitiously gave my dick a few quick pumps. My flaccid 5 incher, became a straining 8 inch dick in no time. Although Paul was definitely not my type, his taking charge and making me feel dominated had an arousing effect on me.

I looked over the Lily to see if she was regretting her prank yet, but she was staring at me in the same way she had stared at the guy in the lobby. When we made eye contact, she shifted here eyes away and pretended to become absorbed in painting.

"Have fun everyone and grab some more wine. Remember, it doesn't have to be perfect, but make sure to get his *ahem* strength to full effect.

30 minutes is a long time, but it went by surprisingly fast. Each time I would start to lose my erection, Paul would dutifully give me a few professional pumps and I would be good to go again. He seemed to really love his job as I got a few pumps when I was still pretty hard. I had to hold myself back from cumming each time, not so much from his touch, but what it felt like to be touching while being watched. All around the room, most of these amateur painters were here not for love of craft, but because they enjoyed nudity. They were staring at my fit chest, the muscles in my legs, and at the length and thickness of my cock. It made me feel strong and desired. I imagined they were just as turned on as I was. And in the case of one painter, a man in his mid 40's with gray but fashionably styled hair, I knew he was turned on by how he couldn’t help but give himself and idle stroke now and again. Between this and the cam sessions, I’m realizing I’m a bit of an exhibitionist.

I rejoined Lily when the time was up, and surprisingly didn’t feel the need to immediately put my shorts back on. "Well I owed you, so there it was. Let's see what you drew," I said, trying to be as casual as possible.

Lily was blushing but trying to play it cool. I could tell she didn't want to betray that she actually might have enjoyed watching me up there in the nude. "I'm not much of an artist so I could only guess what Paul meant by capturing your strength." She turned the canvas to me, and it was pretty clear what she thought strength was. While you make out out my form, the one clearly defined part of the image was my dick coming out of a mess of black hair.

"Oh man. Is that what people see when they see my dick? Is the hair that bad?"

"I don't think it's bad. I actually...thought you have a nice di...penis." Lily said shyly, blushing the whole time.

"He does, and you're a lucky girl to have that to play with" said one of the lesbian women with a funny wink on the way out of the room.

The whole way back to the resort room I felt really uncomfortable. A mix between feeling a horny high from being on display and getting stroked for half an hour without release, and feeling self conscious about having so much pubic hair. All this time being single recently has made me forget the importance of manscaping. Lily noticed that I was off when we got in the room, and in what seemed like a sudden rush, poured herself a doubleshot of rum from the minibar and started furiously rummaging through my things. "Where is it?"

"What the hell, where is what!?"

"Ah ha!" Out came my electric shaver, and I started to put two and two together. Lily offered: "Listen, I think it looked fine, but if you are going to be so annoying about it, then let's just shave it off. Get in the shower."

Let's? I was about to tell her I could do it myself, but the tension in my balls stopped me and forced me to follow her to the bathroom.

"Ok, it's no big deal right? Just drop your shorts and I'll make sure to make your dick something you can be proud of." Lily seemed determined to cheer me up, and I do think a little buzzed from the art wine and tequila shots. It was probably the tension built up all day, but I offered no protest.

I slid my shorts off, revealed my semi hard dick to my sister. Her face was stern with concentration as she approached with the shaver, but her nipples were hard as rocks, and made my dick twinge. "Ok, good," she said noticing the movement. "I think it will be easier if you are hard." Again, she was approaching this like we were solving a problem together, but I was beginning to feel like she was getting into this. I decided to push my luck.

"Well, can you help with that?"

My heart stopped and it felt like an eternity of dead silence. When I looked up, Lily's face had changed. Her eyes softened and her face exuded desire.

"Oh. Does my little brother want his big sister to make his cock hard? Mmmmm. I couldn't take my eyes off you giant dick in class. Come on, can you show me your strength again or should I call Paul?"

My stomach turned with anticipation. "Why don't you make it hard for me."

"Does my little bro like this?" And with that she toyed with the string on her bikini. Although I had already had an eyeful of her tits earlier, the way she was speaking was making me feel hungry for anything she would give me now. I was instantly rock hard as she slipped her top off, revealed her stiff, tiny nipples on her perfect pale breasts.

"Knew that would work!" She laughed. "I was pretty good at talking dirty with Derek, and he liked some kinky role play stuff. Not the first time I've been the slutty sister."

"What the fuck? Was that all an act?" I was a little hurt, not going to lie. Not hurt enough not to still be turned on by her bare breasts that she was now covering with one arm (somehow this was also super hot).

"Hey man, just getting the job done." And with that she walked over and turned the shaver on to start trimming my balls. "Not the first time I've helped someone shave either." With the penis out of the way, she made quick work of my balls. "And now for around the shaft. "

There must be something int he water (or rum) in the resort because without a moments hesitation, my sister put her hand around my dick and moved it down and out of the way to facilitate her work. An electric shock ran through my entire body. I couldn't believe my sexy sister was holding my dick, while topless. I tried to keep still, but could feel my body instinctively trying to rock my hips and pump myself in her hand.

"Lily...I...."

"Shush. I'm almost through."

"No, I..." More waves of pleasure rippled through me as she shifted her grip and gave my dick an unintentional squeeze. The warmth and pressure of her grip and she intense eroticism of being touched by your sister. I couldn't stop it. Before I could utter another word, streams of pent up cum shot onto my sister's chin and chest, pooling between her perky, perfect tits. I don't think I've cummed so hard or felt so fantastic in my life. My knees buckled and I held onto a towel rack to keep from falling. After the waves of pleasure ended and I settled into the after-cum drowsy feeling I always get, I was suddenly reminded of how this happened. With sudden guilt and fear I looked down at my sister, still topless on her knees and who seemed to be frozen. The look on her face was of shock to be sure, but not disgust.

She slowly stood up and, careful not to drip any cum on the floor, walked into the shower. "Well come on and help me clean up, little brother." It was as if those words were now a command I couldn't disobey and I dutifully joined her in the shower and helped her wash the cum from her tits. She seemed to enjoy the command she had on me, and I enjoyed the work. When we were done, we dried off and she looked at me , saying "You owe me another one, little brother. Now get dressed."

Of course I listened. The girl just gave me the orgasm of a lifetime. In my drowsy stupor, I'd kill someone if she asked me to. We got dressed and didn't say much for about 15 minutes.

Lily spoke first. "Lets see what mom and dad are up to. Hopefully dad is in a better mood than before and mom will be happy we are getting along so well." We knocked on the door and mom let us in.

Sure enough, dad had a big smile on his face and looked just as contented as I did in that moment....

Part 3 to follow.

 

Looking forward to it

 

Parts one and two were well done. Looking forward to 3.

 

Great story! Can’t wait for the rest of the story.

 

Very well written and looking forward to part 3 and more!

 

Part 3

"Hi kids! How was the class?" My mom was as cheerful as ever.

All I could do was blush, but Lily came to the rescue, "It was great. Seeing everyone do a normal activity like painting while nude made us a lot more comfortable with being at the resort." Phew. I don't know what I expected her to say, but I'm glad she just kept it to that. She almost sounded like she was playing it up to make my mom feel better.

Lily then turned her attention to dad and added, "Jason even volunteered to be the nude model we all used to paint from. Just standing up there with hard on to demonstrate strength and vigor." She said it so casually, but the way she was directing it towards dad, I know she was trying to get a rise out of him. She's insane.

After a short pause, dad barely flinched and said "Oh, well that's nice darling. Jason, did you have a good time?"

Well that was surprising. Lily seemed annoyed that she couldn’t get dad to react. I was just shocked he was taking it so well.

“Umm, yea it was kind of fun. It wasn’t so bad to be naked since no one else was making it a big deal. And Lily really helped make me feel comfortable too.” There was so much in there I didn’t say. Like the fact that it wasn’t only “not so bad” but incredibly arousing to be naked with others. And also the small fact that my sister unintentionally jerked me off.

“That’s great. I know I was a little worried about everything when we first got here, but hearing that makes me feel better. And your mom spent a lot of time convincing me to relax too while you guys were in the class.”

For some reason, my mom was blushing, and shifted on the couch. “Oh, honey. It was nothing. I’m glad everyone is feeling better. Should we brave the beach and get some drinks?”

"I'm game," Lily chimed in. "Jason, are you going to be wearing a suit, or embracing your newfound naturist lifestyle?"

"Ha ha, very funny." I was not amused. But what came next I can only assume is the mysterious effect that this resort has had on everyone to loosen inhibitions.

My dad looked at us both. "You might have been joking with your brother darling, but actually I want you two to know its OK. Your mom and I talked about it and decided that this is part of what we meant by giving you freedom." His face suddenly turned professorial the way it does when he wants to teach a big life lesson. "You see, for young folks like yourself, its important to test the boundaries...."

Mom swooped in as quickly as she could, "Ok, honey. We don't have a half hour to spare for a lecture on the philosophies of freedom and choice. Bottom line is. Want to be naked? Go for it. And as a heads up, your dad and I will probably be taking advantage of this freedom as well, so don't be shocked it you see us suddenly in the buff! It's something we have wanted to try anyway. Understand?"

I couldn't believe what I was hearing. It was enough that my parents were giving the green light to let me explore the growing exhibitionist in me, but they'd be doing the same! I had resisted sexualizing my mom, but of course couldn't stop myself from peaking at her over the years. Especially with my friends' relentless efforts to try to see her undressed over the years, and their recent tendency to go into graphic detail of what they would do to her if they had the chance. I'd protest, but weakly as I secretly enjoyed the attention she got. Thats right, I'd think, my mom is a MILF. I'm pretty sure my mom was aware of my her reputation, because she would play dumb and announce how pairs of her underwear seem to go missing each time my friends were over.

I side glanced Lily to see her reaction to my parent's decision, but she was playing it cool.

"Very progressive of you guys. Dad, are you really OK with seeing your little ones naked?" There was something almost babydoll coquettish in the way Lily was talking to dad. Mom noticed too, and gave a knowing smile.

Dad blushed a little, adjusted his shorts, and said "Yes its fine. Like I said, your mom made some really convincing arguments for it. Besides. It's a choice. You don't have to if you don't want to. Now, your mom and I are going to get changed. You and your brother go get a spot down at the beach. We'll meet you there. And easy on the booze. I can smell the rum on your breath from here Lily."


--------

We headed out to the beach, passing a pool full of nude swimmers. Again, it was shocking to see how few people took the option of keeping their clothes on. Lily and I got the most stares as we were one of the few clothed ones. Though Lily could draw plenty of attention even not naked. Her pale skin and red hair always made her a lightning rod for attention. She had chosen to wear the one piece bikini she modeled in the store for me, and I couldn't help glancing at her ass as it moved when she walked and at the valley between her nearly exposed tits that I had pooled with my cum earlier.

"Hey, its the stud from earlier!" someone called out. I recognized it as the guy in class who was doing more stroking than painting. I waved, not knowing what else to do.

"Ha. Not exactly the island babe you were looking for I assume. But you seem to enjoy the attention."

In such a short time this resort had helped me feel closer to her and like I can be more open. What's the point of keeping secrets from someone whose had your cum on their chin, right?

"Honestly, I think I really do. It's nice to be noticed and desired. Even from him." I waved again to my admirer.

The beach, much like the pool, was speckled with beautiful (some less so) bodies, glistening with sweat from the pleasant heat. The water looked inviting. Shining shades of blue as far as you could see. The resort was set far enough away from any other place that it made the beach feel more exclusive and private. It wasn't overwhelmed with tourists and peddlers selling cheap junk Like places we have been to in the past. As soon as our feet touched the sand, a young hotel employee named Sean, who couldn't be more than 15, rushed over to assist. He helpfully offered to have us brought some chairs and an umbrella, as well as any drinks or food we might want. We ordered some salads and sandwiches, realizing how hungry we were. And of course, this being vacation, I ordered 4 margaritas and 4 shots of rum. Lily looked over at me disapprovingly.

"What? It's vacation and Im embracing the freedom. Plus relax, some of those are for mom and dad." We found our spot and waved over to Sean who quickly brought us our chairs and umbrella Soon followed another employee with drinks. Lily decided to go down to the water, but I chose to hang back and relax. Really, I wanted a chance to see if there was anyone I would want to flirt with. All over the beach people lazed, sunned, or played in the water. Dad's repeated mantra of "freedom" really started to make sense. I felt so relaxed. Still as horny as ever, but unlike at home, there was a missing tension. Resort magic again, I guess. Pretty soon, a girl about my age caught my attention. She seemed to be with her family as well, and was standing casually, chatting with her father while sipping on a colorful drink.

She was about 5'0" tall, with black skin, afro'd hair that was pulled back to reveal a gorgeous face. Her lips were plump, and her nose stood out as longer than average (I like a good, healthy nose). Despite her short stature, she was stacked. Her breasts stood out, almost a D cup I would assume, with small, dark nipples. When she moved, her breasts swayed from their own weight in a mesmerizing way. Her stomach was toned and flat, but still thick somehow. I think this is what people mean by "slim thick." Her ass, while smaller than my sister's, was healthy and toned as well. Kind of reminded me of my mothers ass. Did I just think that? My god, whats happening? The girl seemed like the most important, delicious thing in the world at that moment. I was instantly sucked in. It was amazing that her father could stand there, both completely nude, and not have a hard on with a daughter like that. I watched her apply sunscreen to her body, making her tits move and sway, and her skin shine in the sun.

“She’s cute, and what a rack!” I heard my mom’s voice from above my head. “Are these drinks up for grabs?” As she said this, my mom moved from behind the lounge chair to stand in front of me.

I nearly spit out my margarita. My mom seemed to glow with the sparking ocean water behind her. She had on a lime green bikini that was so small I felt like I could see all but the most intimate bits of her. Two small triangles covered what seemed like just beyond her nipples and the strings from each went up and met around the back of her neck in a bow. Her bottoms were equally tiny. The bathing suit lay flat against her pussy, and I could see the ocean between her slender thighs. As she sat on a lounge I caught a glimpse of her ass. This was no ordinary bikini. The string disappeared between her toned ass cheeks. Sitting in the sun, just like Lily, my mom's red hair and pale skin shined bright. I reflexively put up a knee to hide my growing erection.

“Mom, did you own that suit?” I couldn't believe she had this hiding in her closet (my friends would have found it by now, I'm sure).

“No. All the suits I had felt too frumpy all of a sudden. I found this in the gift shop and figured it would help me fit in better. Is it ok? Does it look nice sweetie?”

Something about the mix of the intense sexuality of her bathing suit and her maternal use of the word “sweetie” was too much and I had to change the topic before I erupted.

“Where’s dad?”

“Your dad is going to spend all day at the bar, I’m sure. He’s better now, but some rum will help him recuperate from the shock of this place.” As she explained this, my mom knocked back two of the shots, and started sipping on the margarita. “Ooo that’s nice sweetie. Thank you for ordering it.”

I looked back and sure enough, Dad was sitting at the swim up bar at the pool, drink in hand. He was talking to the guy who had been on the shuttle with us with his daughter when we first got here.

We spent the afternoon lounging on the beach. My mom stayed under the umbrella for the most part, afraid her fair skin would burn too easily. Every now and then, Lily would come back and apply some sunscreen (watching her lotion her ass was enough to make me temporarily distract from staring at my Nubian goddess) before running out again to talk to some of the boys on the beach. We ordered drink after drink, and more snacks every now and then. It was fun just hanging out with mom and drinking. When we went on vacation in the states, I was usually left to fend for myself when my parents were drinking, but here I felt like more as an equal. Mom chatted about her work and friends and the continuous stream of alcohol and sunshine began to loosen our inhibitions.

"Jason honey, can you put some sunscreen on me please? I don't want to burn and ruin the rest of our vacation." My mom was laying on her belly in the lounger, and lazily reached back to hand me a bottle of sunscreen. "Really rub it in honey."

"Um yea, no problem." I squirted some in my hands and started at her shoulders. Although she is so slender, her shoulders were surprisingly strong. Her gymnast background really did still come through. I worked my way down her bare back and realized, to my horror and delight, that there was a big issue. I was approaching her sexy, firm, ass. The ass covered by nothing but a tiny string. Even from this close, I couldn't see where it disappeared to. I got my answer when my mom felt me getting lower and suddenly relaxed her legs a bit. They split apart just enough for me to see the string passing over her asshole and broadening into the thicker fabric right before I would get a glimpse of her pussy. Boozy urges threatened to take over as I wanted so badly to bury my face in her ass and to rip her thong off with my teeth. My poor mom. If she knew what her request was doing to her boy, she'd feel so guilty.

I had to calm down. I skipped over her ass and moved to her legs, thinking I could get away with it. My mom didn't flinch and I continued rubbing her down. While Lily's body seemed to be built for fun, with her PAWG ass and healthy sized tits; mom's body exuded strength and grace. As I massaged the lotion into her legs, I kept my eyes on the fabric over her mound and imagined the treasures beneath. I was too horny to care that I was lusting over my mother. In my head I justified it a bit as just an enjoyable view, and I would take that sexual energy elsewhere.

As soon as I was finished with her feet, my mom felt me start to get up and gave a "tsk tsk." I looked at her face to see a smile. "You missed a spot, and I definitely cant have that burn," She said this as she wiggled her ass in the air. My mom, who worked full time, while simultaneously always being the mom who brought the cookies to parent-school conferences, was wiggling her ass at me. Resort magic, I thought to myself again. Without a word, I dutifully rubbed lotion in her ass. It was so firm and gorgeous. I could have spent all day there. I wanted to take a bite, but I forced myself to finish and quickly get back to my chair before she noticed my hard on.

"Thank you. That was nice." She flipped over and did her front side herself.

We chatted for a while longer and eventually my mom asked me about my relationships.

Looking over at the girl with the massive breasts I was lusting over, my mom suddenly asked "What happened with you and your last girlfriend, Sarah? She was such a nice girl. And very sexy too."

I was too buzzed to be overly shocked by my mom's description of my ex as sexy at this point. "She just moved and it was too hard to keep things up. We just bickered a lot toward the end. Also I wasn't getting everything I needed from her," I said, looking over at the naked girl.

"I'm sorry, Jason. Relationships are hard work. You'll be OK. A handsome boy like you. Look how you've grown into such a man." As she said this, she scanned me over and I could have sworn she emphasized "man" when looking at the slightly obvious bulge in my board shorts. I assume the alcohol was taking effect, because her eyes linger and she didn't speak for longer than you would expect mid-conversation. "You know, your father and I went through rough times. But now we really support each other."

They really love each other. It was a nice feeling to still see that in them. "I noticed. He was having a hard time before and you must have said something right, because he seemed totally fine when Lily and I came back."

"Oh, hun. That's easy." My mom started chuckling a bit. "I did what I always do when your dad needs some convincing or cheering up. I sucked and fucked him until all the worries just cum right out of him." And with that she burst out laughing. Did she just say what I think she said? With all the laughing, I couldn't tell if she was joking or serious. Either way, my dick lurched to attention at the thought of my mom on her knees, draining my father. I knew I heard moaning before!

"Mom! Are you serious?"

"Of course dear. When he was good and tired, I just reminded him of all the good that might come from letting you two enjoy your time." We both looked over at Lily at the same time for some reason. Lily was laughing and flirting with a tall and very naked young man. My mom chastised me, "Oh Jason, don't be such a prude. Your mom and dad have a healthy sex life and you should be proud. Plus," she said while gesturing to her body, "wouldn't you be convinced of anything if you had this." Again, she bent over laughing. She could really crack herself up. My mind was too blown to enjoy the sight of the string up her ass when she was bent over laughing like that. Yes, I eventually thought. She could convince me to do anything.

"Anyway, I'm going to go rescue that nice man from your father and make him get in the pool with me. Go find your sister. Better yet, go find a girl!" And with that she left, laughing to herself.

Sadly, the girl I was hoping for was gone. I sat for a while longer, confused and horny, when finally Lily came up. To my surprise, she wasn't with the boy she was talking with before, but with a cute girl.

"Jason, this is Jane. She's form Brazil and here with her guy cousins. She was getting bored so I thought she should meet you."

Jane was about 5'4", with brown, shoulder length hair, blue eyes, tan skin and an inviting smile. Much like everyone else, she was completely nude and unashamed standing in front of me. Her pussy was shaved completely, giving me a full view of her sandy slit. She had a tiny bit of a belly, and round, full tits. Her figure reminded me of what in the past they advertised as the ideal figure of women. A soft and supple body.

I invited her to sit down, and got her a drink. To my surprise, Lily stayed. I expected her to go back to her boys. I shot her a look, but she only winked back at me. We all made small talk and I tried hard not to just oggle Jane's body the whole time. Jane's accent was incredibly sexy, as was the way she laughed at all my dumb jokes. Lily laughed along and kept the drinks flowing. Eventually, talk turned to the resort and nudity.

"I've been coming here for years with my family. We always find the best naturist friendly places." I asked her what she thought about being so open and free with her family. Jane smiled that smile people get when you say something naive and said "my family has always been close. We actually spend a lot of time without clothes in our home in Brazil. It's been that way since I was young and I never felt self conscious about it."

The way she described it was wonderful. I don't know if it's my years of porn or the fact that I don't live in nudist community, but it was hard for me to separate being nude and sex.

"That's so beautiful Jane," Lily said. "I want to enjoy the freedom, but I have to say, being around all these bodies does really make me want to grab the closest penis and go to town."

Jane laughed. "Oh, there are definitely times when I can't help myself. But you two should try being nude while you are here. See if you can enjoy." And with that she put her hand on my leg and looked at me encouragingly.

"Sure, let's give it a try." Lily said. And with that, she stood up and removed her top to unleash her beautiful tits. Several men around us turned to look, as if this is what they had been waiting for. Jane looked on approvingly and then turned to me.

"What about you?"

"I don't know." I could tell she was interested, and I realized that Lily was fulfilling her promise to be a great wingman for me. Jane was right there, and if I went along, I'd probably be able to seal the deal tonight. But the butterflies kicked in, and seeing Lily's tits again made me feel guilty for what happened before. "Im actually pretty tired. We just got in today and I've had a lot of sun. I'll see you around." And with that I got up and left. I could tell I screwed up royally by the look on Jane's face. I could hear Lily trying to make excuses for me, but I moved quickly. As I walked past the pool, I saw my mom and dad, practically intertwined as he carried her around the water with his hands on her ass.

--------

I stretched out in the bed and beat myself up for screwing up a sure thing once again. I barely heard the door open, and soon Lily was sitting on the bed, still topless, looking at me with a sad expression.

"You know you fucked that up right?"

"I know. I told you, this always happens. I get in my head and it all falls apart."

"Well, I told you I would be your wingman, and I'm about to show you the lengths I'm willing to go to help out my little bro. Jane?"

I looked up, and in walked Jane from the living room. They had come back together. Lily explained," I told Jane about your little problem and she thought it was really cute. She wants to help you."

Jane had such a sweet and affectionate expression. She said, "Your sister really cares for you. She reminds me of how we look out for each other in my family. I have two brothers, and we've helped each other grow sexually over the years. I couldn't imagine growing up without them." I started to speak, but she lay next to me and began to kiss me.

Lily looked on. "I think she wants you to shut up before you fuck it up again. Just let us help you, little perv." There was that phrase again - "little perv" - it was so arousing. And her use of the word "us" did register before I felt Jane's tongue snake into my mouth.

We kissed passionately and I explored her curvy body. Her skin was smooth and her tits felt full and perfect in the palm of my hand. She lifted her body up, while pushing me down, and began to remove my shorts. My dick sprung into the air and she looked at it hungrily. "Mmm, you were right Lily. So big. How dare you hide this from me." She bent down and I felt the tip of her tongue trace the shaft of my dick from tip to base and back up again. My hips bucked as my dick begged to enter her mouth. She smiled and continued to tease me, at times just letting her breath excite my member. I looked over and noticed that Lily had moved to the other bed. As she watched us, I could see her hand had moved under her bikini and was moving rapidly, while the other hand was circling her nipple.

The site of Lily was too much, and I surprised Jane by grabbing her by the shoulders and directing her up from my cock. I had her straddle my face with her thick thighs. Jane's legs were so creamy and smooth, and looking up I could see her tits dangling above my head. I buried my face in her pussy and began to explore with my tongue, while supporting her body by placing both hands on her ample ass. She tasted sweet and salty from the beach. I especially enjoyed the smoothness of the inside of her pussy lips as I felt around with my tongue. She moaned and bounced with surprised pleasure each time I flicked her clit with my tongue. She tried in vain to reach back and grip my dick, but the pleasure was too much and her hands just grabbed my arms for support.

From the other bed I heard Lily's efforts increase and her moans get loader. I pushed my tongue deeper into Jane until finally attacking her clit with my tongue. I alternated between sucking hard and flicking with my tongue. Jane screamed in pleasure, and I could feel her thighs tighten around my ears. I realized that with each moan I heard from Lily, I would go harder on Jane. I was putting on a show for my sister. I wanted to show her how much of a man I could be. At this point, my chin was wet from Jane's cum. I knew she was close by the ever increasing pressure of her thighs. Eventually, like rumbling thunder, she let out of moan and I felt her thighs tighten hard. I gripped her ass and continued to circle her clit until her orgasm passed and she loosened her thighs once again. I dove my tongue deep into her pussy, giving her a tongue fucking that would continue to give her spasms of pleasure.

At this point Lily was gone from adjacent bed, and moved to be caressing Jane's back. Lily kissed Jane passionately and whispered to her, "It's time." Jane smiled dreamily. Lily helped Jane move over to straddle over my dick. Although I wasn't tied down, I was helpless to move. Lily had control and there was no way I could fuck this up.

Lily grabbed the base of my shaft while Jane lowered herself onto me slowly. I watched as my dick inched it's way into her pussy. Jane's warmth and wetness enveloped the head of my dick; a feeling that was too incredible to describe fully. Jane took my whole 8 inches, and as her ass met my thighs, her eyes seem to roll back into her head with pleasure. I cupped her breasts and tweaked her nipples, while she slowly rocked her hips.

Lily sat near and continued kissing Jane while stroking her own pussy. Jane and I rocked in unison until she pulled away from Lily and picked up speed. Lily slipped off her bikini bottoms and watched us fuck while sticking two fingers deep inside her pussy.

Jane rode me hard, stopping periodically to bear down forcefully on my dick and rock her hips. In those moments I saw only fuzzy all encompassing lights, as if each trust brought my closer to the almighty.

As I got closer to my limit, Lily moved to Jane and guided her off my dick. Without a word, Jane seemed to understand and got onto all fours, presenting me with her ass cheeks. We were all covered in sweat and I dove in with my tongue again, giving a few lapse to her pussy before rising up to guide the head of my dick to her gaping hole. Meanwhile Jane was busy servicing Lily's pussy lovingly. I thrusted in hard, and Jane's face plowed into Lily's pussy. Lily looked at me approvingly, then closed her eyes to enjoy Jane's attention.

As I fucked Jane's ass I kept my rhythm slow and made deep thrusts while watching the beauty of Lily having her pussy eaten. Her stomach was taught as she held Jane's head in place. She massaged her tits while occasionally giving me lusty stares. I slowed my rhythm even further, fearing I would cum. Soon Lily and Jane's moans grew louder. I could feel the walls of Jane's pussy tighten around my cock and I instinctively knew to pump her harder. I could hear Lily's moans getting louder and more intense at the same time. Lily went first, screaming in pleasure and within seconds, I felt Jane's body push hard into my hips, digging my dick so deep into her that I could hardly thrust. Not wanting to let go of Lily's pussy, she moaned in orgasm with a full mouth until her body relaxed.

As I was about to begin slowly pumping again, Lily guided Jane's body away from my dick. I looked at her questioningly, and she purred, "I want it like it before. Please." As she said this, she pushed her tits together, looking at with me pleading eyes. She and Jane were on their knees, taking turns licking Jane’s cum from my dick. Eventually Lily put half my shaft in her mouth and swirled her tongue around. She released and Jane did the same. My balls tightened and threatened to burst. Lily sensed this and took me into her mouth and encouraged me without words to fuck her face hard. I wasn’t going to last long as the pleasure built to maddening heights and the site of my sister and our voluptuous plaything was too much to bear.

I pulled my dick out and Jane stroked me hard, pointing me towards Jane’s waiting breasts and face. I locked eyes with Lily who opened her mouth and waited.

It felt like it came from deep within me. Unbelievable, warm, all encompassing pleasure. As I shot ropes of semen into Lily’s waiting mouth, Jane slowed and tightened her grip slightly. Not to be left out she moved me to spread my seed into her mouth as well. Lily, whose mouth dripped with cum that flowed down her chin and onto her chest, looked at Jane with hunger and jealousy. She began to kiss her and grope her, spreading my semen all over each others bodies. A tangled, erotic mess of fiery red and soft brown hair. Lily continued to kiss her deeply, seeming to want to wrestle the stolen semen from Jane’s mouth.

I lay back too exhausted to stay on my feet and watch them, but the girls soon joined me at the top of the bed. We lay together, lazily caressing each other. In the dream-like state I had no idea whose hand was tracing my now flaccid penis. Looking down, I noticed for the first time that Lily was not shaved completely. While her pussy was as bare as Jane's, she kept a tapered rectangle of short red hair. I idly ran my fingers across the patch, enjoying the full body relaxation post-climax.

After some time, I couldn't be sure how much, Jane got up and made her way to the door. I invited her to shower with us, but she said something about her cousin's enjoying rounds of sloppy seconds.

Jane and I continued to lay in bed, not saying a word.

Part 4, coming soon- From the perspective of Dad.

 

Great job, like the story, well written great proofing - very verr few errors (if any), unlike many stories that are riddled with gramatical, diction and or vocabulary errors, this story does not suffer from these errors and stays tense correct! Great job!

 

Loving this story, cant wait for more!

 

eagerly waiting part 4

 

The wait is killing me

 

Excerllent!

 

Great story!

 

Part 4 - Picking up after getting a look at the hotel room for the first time.

“I’m going to take your father to the room to unpack and settle him down a bit. Why don’t you kids get comfortable and look for that class. We’ll meet back together for dinner.” And with that my wife Diane pushed me through the adjoining room door and left the kids to their own devices.

I slumped onto the couch. My daughter Lily's voice teasing me about all the nude people on the beach rang threw my head. What have I exposed my sweet little girl to?

"It's going to be fine, John," Diane assured me. "I was serious about what I said. The kids will really get to explore their independence. Jason needs the confidence and Lily...well Lily will just enjoy it." As she said this, she poured me a giant glass of whiskey and handed it to me. "Drink this," she said, with a slight command in her voice. I took the glass and gulped.

"I can't believe the situation I've put everyone in. My friend from work takes his kids here! He had to have known." I took another gulp and felt the sting of the strong drink.

"John," my wife called, but I was too locked in to my worries to even turn. "John..." I looked over and nearly spilled my drink. Diane had stripped off all her clothes, and was leaning seductively back against the hot tub. "I think I know how to make you feel better." Indeed she did. This was always her go to move. Anytime I needed convincing of something she knew exactly how to get me into a pliable state of mind. Like hearing a siren's call, I knew what I was being pulled into, but my stiffening dick led the way. "Now take off your shorts," she purred as she slowly walked toward me.

Her graceful pale body, with perky tits, taut stomach and toned legs moved beautifully. I obeyed and stripped down, taking off my shirt as well. Diane knelt before me, looked into my eyes and wrapped her lips around my cock. Her tongue snaked around my 8 inch shaft, and warmth and wetness made me want to fuck her face right there. I held back and let her do what she wanted.

If only the kids could see their sweet suburban mom now, I thought. Few knew the kinkier side of Diane. Going all the way back to high school and up until the kids were young, Diane was the guiding sexual force of our relationship. In high school, she delighted in teasing our teachers with downblouse stares and accidental upskirts. We would fuck after school thinking of all the people who were dreaming of taking her for their own. Recently, she had taken up something similar, but this time with Jason's friends. She would intentionally not wear bras, or would leave used thong panties around for them to find. She would encourage me to play along and point out how hot some of Lily's friends had become. She had taken to teasing me during pool parties of stealing glimpses of their young, bouncing bodies.

As Diane slowly enjoyed my cock she kept one hand on her own clit, rubbing rhythmically. Eventually, when she felt me start to buck, pushing my cock deep into her throat, she gave me one quick deep throat and pulled me out. Diane turned around so that I could enjoy the view of her amazing ass, and slowly sat on my lap. Her ass has not changed even a little since high school, when she was a gymnast. She rocked her hips, letting my hard cock rub on her pussy lips without entering. The wetness and teasing was intoxicating. "Mmmm honey. Just think of what this resort could give us. So many people watching me, wanting me. And you can finally get what you want..." As she said this she lifted herself slightly and reached back to grab my shaft.

"Mmmhmmm, what's that baby."

She brought my dick to the edge of her pussy, putting the tip in just at the edge and circling it around a little bit. "To finally see how your little girl has grown into a very fuckable woman." Before I could even react in shock, Diane pushed back hard and slammed me into her. The feeling of her warmth enveloping my entire cock was intense and all I could utter back was a yell of pleasure. "I've seen you catch glimpses of Lily's gorgeous ass. I've watched you lust over those perfect tits of hers." As she said this she continued to work my dick, fucking me hard. I was helpless to move. A slave to the pleasure of watching her firm ass pound into me as she invoked visions of my daughter's body. I knew instantly that she was right. In my heart I knew that so much of my protests and worries about being here had to do with being confronted with my desire for Lily. Knowing my wife knew this, and better yet, enjoyed this, was so arousing I felt like my dick grew an extra inch inside of her.

As Diane continued to rub her clit and pound me hard, I took over and grabbed her hips aggressively. I slammed myself into her and Diane arched her back in ecstasy. "Yes!" she screamed as I fucked her. Each trust a validation of what she had said. "Fuck me like you want to fuck her. Say her name."

"Lily!" I moaned. Hearing my daughter's name seemed to pushed my wife over the edge as she rubbed her clit harder and I felt her pussy tighten around my shaft. Her body shivered as I felt the orgasm go through her.

"Yes, daddy!" she purred, pushing me over the edged. I pulled out and sprayed my cum all over her perfect ass and back. I collapsed next to her as she lay on her stomach, both of us on the floor panting in pleasure and exhaustion.

As I lay there, in that state of full body exhaustion that always follows amazing sex, I looked over at my wife. Diane laid there in the same bliss state, my cum still pooled on her lower back and across her ass. "You're really OK with me leering at our daughter?"

Diane smirked, and still with eyes closed said "Oh please. Let's call it admiring. And if it makes you more comfortable, I'll be doing the same to Jason. If you hadn't noticed, I think he's taken after his father in the size department. Now get up and and come to the shower. You've made a mess of me and now you have to clean it up."

------

After a refreshing shower and steam, the kids joined us in the room. They seemed to really have enjoyed their class. Lily took the opportunity to try and get a rise out me by mentioning Jason's nude modeling. Before "talking" with my wife, i would have been thrown for a loop. But now I thought I recognized something else. Lily's constant teasing of me felt almost like flirting. When I didn't have the shocked reaction she was looking for I could tell she was annoyed. Hearing the story of the class made me just happy that this place seemed to be bringing Jason and Lily together more, even if in very untraditional ways. We made plans to meet them on the beach, and Diane and I finished getting ready.

We eventually made our way out of the resorts lobby and after a quick stop at the gift shop so Diane could get a better bikini, we walked toward the lavish pool and shining beach just beyond it. "I think I need some time at the bar before I brave the beach to really let this all sink in.," Diane was happy enough with that and made her way to the beach. I enjoyed watching her walk away in the string bikini, and so did a dozen or so other men and women sunbathing on the pool deck. "She's still got it."

I jumped in the pool and swam up to a stool at the bar. The water was just slightly cooler than my body, the perfect temperature for a pool. I ordered another whiskey and the bartender gave me as healthy a pour as my wife had earlier. I had to remember to pace myself otherwise I'd be sun and whiskey drunk in no time. To my right, I noticed the stark naked body of the man who had rode in on the shuttle with us earlier today. He was a man in his early 50's, with salt and pepper hair, a short stubbly beard that was trimmed rather than neglected, and the slight pouched belly that often came with his age. Between his legs drooped what appeared to be a healthy sized penis with trimmed back hair. Trying to be friendly I introduced myself and he introduced himself as Michael. We chatted and drank for a while and found that we got along relatively well. "Weren't' you here with your young daughter?" I asked.

"Oh yes. Though she's not as young as she looks. She was blessed with a youthful appearance for sure, but the braces always throw people off. She's just turned 17. We come as often as possible since she loves it so much. It's really helped us get closer since her mother died." I expressed my condolences and he tanked me.

"Honestly, this is my first experience at a place like this and it's great to see that it can bring a dad and daughter closer." I genuinely felt a small weight lifted from my shoulders in speaking with him. He had a calm and gentle demeanor.

He gave a smile. "I totally understand. We have always practiced nudism in the home and so places like these are just an extension of that." We both took a sip of our drink. "You seem like a nice guy, and I believe in this lifestyle enough that I want it to go well for you. Why don't you come by tonight for dinner, and Stephanie and I can answer any questions you might have."

"I'd really appreciate it. I'll let my wife Diane know."

When Diane returned from the beach she seemed to be in good spirits and was delighted to hear of our dinner plans. After a swim, we returned to the room and called the kids to let them know they were on their own for dinner. I was surprised that they didn't protest, but instead said they already ate plenty and were heading to bed early. Jason sounded truly exhausted on the phone.

-------

Diane and I took the stairs up the the top floor of the 5 story resort. We walked toward the end of the hall and knocked on his massive door. When Michael opened the door and let us in to his penthouse suite I was immediately taken aback by the space and luxury. "Jeez Michael, this is great."

Michael just laughed in an unself-conscious but gracious way. "Perks of coming here so often. The owners are great people and we've become pretty close." Make yourself at home and I'll get Stephanie so we can sit and eat." Before he left to the other room he handed Diane and I a glass of wine.

"Nice guy," Diane said with a smile. But her face was a little concerned. "I kind of feel bad. Is it just me, or has wearing clothes in a place where everyone is naked started to feel a little rude?"

"Honestly, I feel the same way. But what are we supposed to do? Just strip and toss our clothes in the corner?" I joked.

"Please do if it would make you feel more comfortable." Her voice was sweet and when I turned around to see Stephane, the view was even sweeter. Stephanie was about 5'1'', with long blonde hair, a delicate face, sparkling green eyes, and a deep brown tanned skin without a hint of tan lines. Her hair draped over her collar bones and stopped just above two perky handful sized breasts. He stomach was flat but soft and her pussy bare of any hair whatsoever.

"Nice to meet you Stephanie. My husband and I were just saying that maybe it's best we join you in the buff. Your dad was kind enough to invite us since this is all so new."

"Why don't you two head to bathroom so you can work yourself up and come out however you choose. No need to strip here in the foyer. When you're done, join us at the dinner table." Michael offered.

Diane took my hand, not bothering to allow for any protest by me, and made her way to the bathroom.

Once inside, I asked "are you sure?" But she was already kicking off her shoes and pulling off her shorts. She wasn't wearing any underwear. I should have guessed she knew where this was going before we even left our room.

"Of course. We wanted to do this at some point in our lives, and here's a chance to experiment with it without the kids here. Now get your clothes off."

I went along, half because I couldn't resist her, and half because I knew I wanted to as well. OK, maybe I could also admit that I'd enjoy letting Stephanie get a full view of my dick too. One minute later, Diane and I exited the bathroom stark nude and trying not to be self conscious. We made our way to glass top dining table where Stephanie and Mike were already seated, both enjoying some wine. Diane and I sat and the conversation flowed easily. I noticed how close Stephanie and Mike seemed to be, and ever registered the way that even nude, they touched each other with affection. Not a hint of hesitation or embarrassment as a result of their nudity was evident.

After a time, Mike broke the ice. "So how are you two feeling. Being nude and all?"

Tired of having Diane speak for both of us, I piped up. "You two are so in-sync with each other, it's hard to feel any other way than comfortable." Diane smiled and put a hand on my leg which made my dick twitch involuntarily. The twitch might have made me more attentive to the beautiful young girl next to me. "Stephanie, whats it like for you?"

Stephanie gave a shy smile. "It's nothing really. We've had a very open house since I was young, so seeing my mom and dad naked, and being naked with them felt natural. Going to school is the first time I really understood that not everyone lives so freely. But I always imagined the other kids would be jealous if they knew how we lived."

"That's so nice to hear. You seem like such a sweet and good natured girl. I feel like maybe your lifestyle helped with that," Diane added.

"She's always been this way. Open minded and curious so nothing in the world could frightened her. I watched her peers go through the stress and tension of sexuality during their teen years, but Stephanie has sailed through, having seen and asked about everything from a young age."

"Seen?" I asked.

"Oh yes," Michail said, a little surprsed. "I thought it was clear. Part of the openness is being open sexually as well. No locked or shut doors meant Stephanie got plenty of chances to watch her mother and I make love."

Diane's hand on my leg tightened slightly and I saw her legs move slightly apart. Thinking of this young girl watching her parent's enjoy each other made my dick raise to half mast. Stephanie laughed. "Dad makes it seem so simple. But trust me, when I really understood what it meant to have sex and give yourself to someone like that, there were some awkward moments." She looked at her father tenderly. "But since I didn't grow up with the shame my girlfriends had around sex and their bodies, I felt free to go right up and talk to my parents about it all."

"Well that must have been hard to know what to do, right Michael?"

"At first, but eventually we figured out that in the spirit of openness, Stephanie should learn through experience if she wished, rather then us explain it awkwardly. I still remember the first time she joined my wife and I in bed and held my penis in her hands. She marveled at its thickness and asked a million questions. She didn't let it go all night!" Stephanie laughed at this, as if she too were remembering that night fondly.

Suddenly, Stephanie reached over and gripped my penis gently in her hand. "I remember thinking, my goodness! How does this whole thing fit in mom's mouth!" She laughed as if it was the most natural thing in the world to grab someone's penis. I was instantly rock hard, and Diane gave a little gasp. I looked to her, worried how she would react, and half trying to understand how I should react, but I saw that she was staring intently at the little girl's hand around my cock, while one of her hands was gently fondling her own mound. Mike looked on the scene affectionally.

"We showed Stephanie everything about our bodies and let her fully explore. It was quite a thing to see." Not letting go of my penis, Stephanie reached over and held her father's cock in her small hands. “John, you’re so thick compared to my dad.” I could feel her hand giving light squeezes and rubs to my penis, almost absentmindedly. I had to assume she was doing the same to her father's dick. The sight of her holding both of us was intensely erotic and I dared not say a word for fear it would break the moment. Her arms were spread, holding us both, and her nipples were hardened on their small hills. I wondered if her seat was wet from arousal. I was in fact dying to find out.

Diane broke the silence by asking, “Stephanie, can you show us what you’ve learned? John's been thinking about teaching our daughter to be open too.” I looked at her with a shocked expression. Not because I disagreed but because Diane continues to speak from my own inner desires.

“Of course. Is that okay daddy?” Stephanie asked her father.

“Yes sweetie. It’s why I invited them in the first place. Show them what a good girl you can be.”

And with that, Stephanie began stroking her father and I slowly. She was in no rush, and appeared to be enjoying herself. Mike simply sat back with his eyes closed and a contented smile on his face. I had a feeling this was a near nightly occurrence for him. Meanwhile Diane had moved closer to me and began to kiss me deeply. I fondled Diane’s breasts while Stephanie continue to pleasure me.

After a short time of Stephanie’s gentle handjob, Mike opened his eyes and said “Maybe we would be more comfortable in the bedroom.”

He stood up and took Diane’s hand. They led the way and Stephanie and I followed. I could barely make out that Diane had begun to stroke Mike on the short walk through the lounge and into the bedroom. Stephanie simply smiled her shiny smile at me and complimented Diane’s body. “You’re so lucky. I hope my ass looks that good one day.” I reached back and stroked her small but smooth ass.

When we got into the bedroom Mike was seated at the edge of the bed and Diane wasted no time getting on her knees to suck his dick. Stephanie guided me to sit beside Mike and got on her knees as well. I became intensely aware that my naked skin was touching Mike’s. I had never been this close to a naked man before in a sexual context. But before I could process anything, Stephanie began to service my cock by traveling up and down with her tongue while gripping my balls.

“Good girl,” I heard Mike utter. Apparently he did not want to miss the chance to watch his daughter take me into her mouth. Diane had switched to stroking Mike's cock in order to watch Stephanie too. Soon Stephanie lifted her head slightly and engulfed my cock in her tiny mouth. I saw her lips bulge as they tightened over her braces and she moved in rhythm. It felt incredible. Mike shifted Diane to the bed and got down on his knees to eat her pussy. Father and daughter serviced their guests side by side. I turned my head to kiss Diane and look at her appreciatively. She had begun to sweat and her body glistened as her stomach tightened with pleasure and her legs were lifted and bent. I love her slender pale body and it felt special to see it this way. I had never seen her body in the throes of sexual passion from the outside before. It was magnificent.

Stephanie took her mouth off my penis and moved onto the bed. Without saying a word, she knelt on Diane’s face and allowed Diane to devour her bald mound. Diane lapped at her and sucked her clit happily. I watched contentedly until Mike stood and guided me on to the bed as well. He and I stood on either side of Stephanie's face. Mike put his hand under her chin and directed her mouth first to my cock. With eyes closed, Stephanie took my entire length, then moved back and forth between her father and I. She held both of us in her hands, pulled us closer until our tips at times were rubbing together. The sensation was thrilling and the sight even more so, as Stephanie worked to pleasure us both at the same time.

Soon the pleasure of this young girl's mouth became too much and I pulled away. I didn’t want to cum yet. I moved down to Diane and fingered her hole and played with her nipples while watching as Stephanie deep throated her father. “Mmm baby. You’re doing such a good job,” Michael encouraged.

In my hand I could feel Diane tensing and getting close to cumming. While keeping my fingers inside her, I bent and began vigorously sucking on her clit. Diane moaned into Stephanie’s crotch and flexed her abs in the ecstasy. She orgasm rumbled through her entire slight frame and caused her to stop eating Stephanie out. Stephanie watched the display below her while stroking her own tits. Mike moved down the bed and was stroking Diane’s breasts. All three of us were attending to her. Soon Diane’s body relaxed and she left out a soft contented sigh.

“Steph honey, will you let John finish in your pussy while I finish in your mouth?” Mike asked as simply as if he were asking her what dinner she’d like that night.

“Of course. I've want to feel that girth inside me.” Stephanie got on all fours, and to my surprise, Mike grabbed the shaft of my cock and guided me into his daughter. The feel of his hand shoving me into her was so new that it had an intensely arousing effect and I strained to stop myself from exploding. I held myself motionless inside his little girl, feeling her extremely tight pussy surround my dick. I felt I could have stayed still there all day, but Mike had moved to Stephanie’s mouth and began to thrust into her. This movement pushed her body back and forth slightly over my penis and I began to involuntarily rock my hips to fuck her.

Diane had recovered and joined me at Stephanie’s ass. She smiled as she held the girls cheeks and tried to control their rhythm on me.

“Slow, slow,” I urged. “I'm about to burst.” Diane obeyed and held one finger finger over Stephanie’s asshole as she moved her into me gently. Stephanie must have felt this and reached back to take her own wetness from her stuffed pussy, and then came around with that hand to guide Diane’s finger into her remaining unstuffed hole. Diane followed through and fingered her puckered hole, causing Stephanie to flex the walls of her vagina onto my cock. I had never felt such tightness before. I couldn’t take it anymore and began pounding her like an animal while trying not to knock Diane’s hand out of the way.

Stephanie screamed in pleasure and soon both of us were climaxing at the same time. I filled her deep with my seed and her vagina gripped my penis tightly as if trying to coax out every drop. I held myself inside her as a Diane removed her finger from her ass.

“Can’t forget about you,” Diane offered and moved to our host. In the throes of orgasm, Stephanie had stopped sucking on her father. Diane stroked Mike’s dick hard and held Stephanie’s face up by the chin. Stephanie smiled a braces-full smile and opened her mouth. I pulled myself away to get a better view just as Mike began shooting load after load of thick semen. He coated his daughter's braces and face with his cum. Stephanie accepted this gratefully and moved her tongue in a circle to clean her lips off and swallow her fathers offering. Mike smiled approvingly and stroked her blonde hair paternally.

We all collapsed on the bed. The smell of sex hung heavy in the air. I held Diane close and ran my fingers over her smooth pale skin. “I love you honey and I’m open to whatever this resort brings us.”

After some time of silence Michael lifted his head and asked, "So who's hungry?"

Part 5 to come soon.....

 

This is a great series so far, great work.

 

I’m enjoying this series