Family Trip to Jamaica Part 7 by robdcruz

That’s weird, Lily never came home. But soon I noticed a note on the nightstand. It was Lily’s writing.

“Hey perv. Nice job sleeping with your junk out. You were passed out cold, so I didn’t bother waking you. Looks like you worked yourself into a coma. Find Jane again? Can’t wait to hear about it. Mom and dad left early to have the day to themselves and I didn’t feel like waiting for you so I’m off to the spa again. You’re on your own.”

Spa again? Typical of her on vacation. She must have really enjoyed her time there yesterday.

I’m was a little miffed that I’ve been left alone, but realize soon that I was really upset that I wouldn’t be spending time with two of the women who will give me the best chance of getting laid. There’s something exciting about being around someone you know you could just fuck in the other room, given the chance.

Unsure of what else to do, I set my sights on heading out to the beach and enjoying the sun. I made a quick trip to the bathroom to brush my teeth and have a quick rinse in shower, then went to get dressed. I was hit with the liberating thought that I no longer had to bother getting dressed. How freeing. I can just walk out of this room and stroll to the beach without a stitch of clothes on.

As I was about to open the door there was a sudden knock that startled me. I am even more shocked once I open the door to see Alex on the other side.

“Hi again!” she said cheerfully. She looked as cute as ever, but seems different from the day before. It took me a second to realize that she was fully clothed. I’d become so used to seeing her naked it was a shock to not see her tits. She was dressed in short blue denim cut-offs that showed off her thick but toned legs, a red t-shirt that tried its best to contain her breasts, and her hair had been dreaded into two braids running down either side of her head. While I did love seeing her naked in all her glory, seeing her with clothes on cemented how attractive she was all around.

“Hey,” I said, feeling shy and realizing how being the only one naked can can make you feel awkward. “What’s up?” A sudden feeling of dread hit me as I worried that her wearing clothes meant she was leaving the resort.

“Well, I had a ton of fun at the show yesterday and was going to wait for you at the beach to plan our dinner, but you were taking forever. Are you trying to make me chase you?” she said with mock disapproval.

“Ha, no. I’m just exhausted and overslept I guess. What’s with the clothes?”

“I know, weird right?” she said looking down at her outfit. “I was thinking that instead of a boring dinner, we could head out to the city and explore a bit together. Are you up for that?”

Spending the day with a girl I thought was way out of my league? Internally I was jumping for joy and screaming ecstatically. “Yea, sure. Sounds cool,” I said as nonchalantly as I could. “Come on in while I put something on.”

I got dressed and Alex and I got on the shuttle into town. The conversation between us was easy and fun. I had to assume that despite not having spoken more than a few sentences to each other yesterday, being nude with each other earned us some instant level of intimacy. I found out that she was from New Jersey and had been coming to the resort with her parents for several years. She used to come with her mother and father both, but her mother lost interest after her parent’s divorce. So for the last couple of years it had been just her and her father.

Alex knew the town pretty well, and was a dutiful tour guide. She took me to see some of the local markets for random souvenirs, but got more serious and took me to some local sculpture and art galleries. As she spoke with knowledge about the art, I couldn’t help be impressed and turned on by her. I had been so focused on how incredible she looked on the outside, that had it not been for this trip, I would have neglected her inner depth.

Over lunch, with some of the best fish I’ve ever eaten, we drank heavily of the offered rum and I felt my courage building to ask her a question that had been on my mind.

“What’s the deal with you and your dad?” I asked, more bluntly than I had intended.

“What do you mean?”

“I mean, for my family this place was an accident. We didn’t mean to end up here and certainly didn’t mean to be opening up to each other the way that we have been.” I left it vague as to the ways we were opening up exactly. “What was it like for you guys? Were you always that..comfortable with each other?” I thought back to how her father had been stroking his hard on while watching Alex dance for me, and later how it pressed up against her naked body when she jumped up to give him a hug.

“I get what you are asking. It must seem weird for you to be first experiencing it now, so grown. For us, nudity just wasn’t that big of a deal around the house. We didn’t really seek out resorts like this, but we were definitely open. Before things got bad with my parents I walked in on them having sex plenty of times. It kind of loses its shock value after a while.”

I guess that made sense. I tried to think back to if I had ever seen my parent’s fucking. I was sure I hadn’t ever seen anything, but I did have vague memories of the sounds of commotion and groans from multiple people when Lily and I had gone to bed when I was younger. The thought of my parents having sex might have made me feel weird before, but now I was seeing that there was a part of me that would welcome it. I want them to be happy. Plus, anything involving my mom and sex is OK by me. At least since last night.

The rum was really getting to my head because what came out next from me surprised even myself. “It was definitely a shock watching him stroke his dick in the audience while you gave me a lap dance though!” I tried to laugh to lighten it up as a joke, but it came out awkward and forced. Immediately after saying it, I regretted it.

To my surprise, Alex just smiled. “I know! He’s so brazen about it sometimes.”

“You knew!”

“Of course. You don’t grow up in an open house and not see a hard on every now and then,” she said.

“Sure, but he was really going at it. You had to have felt weird when you hugged him and it pressed against you.”

Why was I pushing so hard on this? Was I really so curious? Or maybe I was just grasping for anything to help me feel better about my own blurring of the family boundaries. And, it was a bit of a turn on to hear about her dad jerking off to her.

“I definitely noticed that. He’s huge after all. What’s so hard to get. He was aroused and that’s just what you do when you are horny. You take care of it, or get it taken care of. It wasn’t a strange thing to see my mom or dad get horny and jerk off or fuck, just so they could get on with whatever they were doing before they were horny. It just makes sense.”

There was no question that I was now asking because it turned me on. I felt my pants get tighter and tighter and had to resist rubbing the outline of my dick through my shorts.

Alex noticed me shift in my chair and got a look in her eye. “That’s nothing. My parent’s wanted me to be prepared to make good, healthy sexual choices, so eventually I didn’t just walk in on them, I was invited in.”

I nearly spit my rum and coke onto the table. “Invited in? Like you joined them in bed?”

“No, not really. I would come in, and they would just show me stuff. How to give a hand job, a blow job, how penetration worked up close, how to get your pussy eaten, and even anal if I ever wanted to.”

I couldn’t take it anymore and tried to discreetly graze my cock under the table. Alex poured me another shot. I noticed that she had a hand under the table as well. Was this turning her on too?

She continued. “After mom left, my dad really struggled. Not only had his wife left, but now he had to take care of this teenage girl who was growing and maturing-” as she said this she looked down at her chest. “-and he had no one to help him out. So one day when I knew I had made him hard I felt so bad I offered to take care of it for him. Since then, anytime I wanted to, and he needed to, I got a first-hand education.”

I couldn’t tell if she was telling the truth or if she was making this up just to torture me.

Her mischievous eyes turn softer. “Poor guy, you must be aching. Want to go back to the resort and take care of your ‘big problem’ right now?”

“I thought you’d never ask.” I rushed to leave, putting far too much money down on the table for the food in my hurry. I just needed to get home and fuck this girl so bad.

In the shuttle on the way back to the resort, we pawed at each other and kissed intensely. Alex’s hands roamed over my shorts and caressed my straining cock while I spent some time feeling her up. There was something so different but extremely sexy about making out with clothes on that I had missed yesterday when I was buried in her tits during the strip show. As I groped her, the anticipation of getting to see her, and taste her, kept building.

By the time we got to the resort I was drunk with passion. We rushed quickly to my room. I fumbled to get the door open and suddenly felt her pushing against me. I dropped the key but didn’t care. She pushed me against the wall, and we continued to kiss there in the hallway. She shoved her hand down my shorts and gripped my cock as she kissed me, stroking it as best she could with my shorts on. I let my hands roam and massage her ass.

When I couldn’t take it anymore, I grabbed the key from the floor and entered the room. I was nearly dragging her to the bedroom when I noticed the adjoining door open. As I approached it to close it I heard muffled groans and grunts. I slowed down and pulled the door slightly more open. Alex and I peeked in and I let out a small gasp of surprise at what I saw.

I recognized Lily’s body, bent over the hot tub, flushed red and sweaty with effort and arousal. Her red hair was disheveled and covered her face as she bent over. Her tits were hanging down and moving to the rhythm of the pounding my father was giving her from behind. His legs and back were flexed as he put all his effort into fucking my sister hard. Both his hands gripped Lily’s ample ass and occasionally would give them a hefty slap. With each slap, Lily would give an excited yelp then return to groaning in ecstasy. Neither of them seemed aware that Alex and I were watching from the doorway. As the groans grew louder, Lily exclaimed, “Oh, daddy. Yes, daddy!”

Alex stood in a near trance, watching intently. “Oh my god. That’s so fucking hot. He is really taking her hard.” She looked back at me and was startled by my expression. “What’s wrong?”

While the sight of my sister being taken from behind was extremely sexy, I couldn’t help feel confused and jealous. My sister and my dad are fucking? When did this happen? I was aware of the fact that I had fucked my mother, but somehow put that aside as situational and different. “I have to get out of here,” is all I could muster, and rushed out of the room.

Alex followed me out to the hallway, completely confused and trying to help calm me down. I walked without purpose to the lobby, unsure where else to go. Alex began pulling me toward the elevators.

“Come on. You need to lay down.” She hit the number three in the elevator, and got me to what I assumed was her room. “Don’t worry about my dad. He’s spending all day at the beach.” The room was identical to ours. Despite the cloud of confusion and emotion over me, I still made a note that there was only one bed for both father and daughter.

Alex led me to the couch, then went to the room’s bar to make us each a glass of something strong. The sting of the alcohol was a welcomed change of feeling, but I still couldn’t wrap my head around what I saw.

Alex sat close to me and asked, “Want to tell me what this is all about? Did you know those two?”

“My dad and my sister,” I said flatly, staring at the ice in my drink. I knew after everything we had shared she would understand.

“Oh,” Alex said with slight surprise. “I’m guessing you didn’t know they’ve been fucking? She put her hand on me knee. “I can see how that’s confusing. It’s so new.”

“It’s not just that,” I told her. I knew exactly what it was, but was having a hard time admitting it. Knowing Alex has an open family did help me feel better though. I felt like I could trust her to understand. “It’s not just that it’s new. I… I was angry at seeing my dad with her.”

A looked passed over Alex and I could tell she understood. She scooted closer to me on the couch and I could feel her body pressuring against mine. Her hand on my knee shifted ever so slightly, but the shift signaled something more than just concerned care. “You were jealous of him, weren’t you,” she said, with a slight sultriness in her voice.

“Yea, I was.”

She moved her body even closer into mine, which I didn’t think was even possible. Her mouth was next to my ear, almost touching it. “You wanted to be the one to fuck your sister, didn’t you.” When I didn’t protest, she went on. “She was so hot, bent over that tub. Her beautiful red hair was wild in her face, and your dad was so lost in his lust for his little girl.” As she said this she pushed me back on the couch and straddled me. My earlier confusion was being overtaken by arousal.

I looked up at her face and could see the lust she was talking about mirrored in her own eyes. I was being drawn so deeply into whatever Alex was doing, all I could do was nod and enjoy the pressure of her body against my crotch. My dick grew harder and I knew she felt it.

Alex started to slowly grind me while saying, “Maybe you just need to take your mind off her a little bit.” As she said this she lifted off my shirt and I gave no resistance. The feeling of her smooth, dark legs against mine was so sexy. Thoughts of Lily’s sweating body being pounded by dad were fading into the background.

Alex ran her hands over my bare chest, enjoying the feeling of my muscles. As she used her hips to make circles on my dick, she ran her hands over my shoulders and moved her tits, still in the shirt, closer to my face. I took her in and for the first time noticed she smelled like lavender.

Alex stood up and bent her knees in a kind of crouch to pull my shorts and boxers down, so I was left on the couch completely naked. My dick, not yet at its full length, was standing up stiff. I began to reach up to give it a stroke, but Alex swatted my hand away. “No touching yourself and no touching me unless I tell you it’s ok.” Again, all I could do was nod.

Alex walked away and kept her back to me as she swayed her hips. Although no music was playing, I felt as if we both understood the beat of the music she was moving to. She stopped suddenly, put her legs together, and bent straight down at her waist so her ass stood out prominently towards me. She unbuttoned the shorts then hitched her fingers in the belt loops and slowly slid them down her sexy legs. She was wearing a thong and when bent over I could see her mound covered by the cloth. My dick raged and begged to be touched but I obeyed her earlier command.

Without looking back, as if she was moving for her own pleasure only, she slowly moved her legs out so I could see a gap between her thighs. Her ass so was impressive and gorgeous. She began to give it little shakes by pouncing her hips. Her ass clapped hypnotically and made me want to bury my face in it.

Alex turned to face me and looked down to smile at my aching cock. “Enjoying the show?” I nodded as I scanned her body. The strings of her thong rode high up on her hips and barely covered her pussy. She moved in a way that opened up her legs and gave me more of a view, teasing me with something I could not yet touch. Yet.

Alex then lifted her tight shirt, which caught under her massive tits. Her stomach was thick but flat and I wanted nothing more in that moment but to put my lips to her. The more of her skin I saw, the more I wanted to devour her. I could spend hours licking and kissing that skin. With her hands on both sides lifting her shirt, she began to shake the shirt, causing her massive tits to bounce. I could tell she wasn’t wearing a bra by their movement and waited desperately for the reveal. Slowly she lifted the shirt up, giving me a view of the underside of her tits. “You like these?” she asked.

“They’re incredible,” I responded. My eyes were fixed on the spot where her shirt met her tits.

Alex grinned and put her hands down, leaving only the underside of her breasts exposed. Such a tease. She moved her hands over her body and caressed her pussy and covered breasts as she walked closer to me. She bent forward and thrust her chest into my face and I made every effort to bury myself into her, but she quickly pulled away. Alex once again straddled my legs, pushing her pussy against my dick. Mercifully, she reached up and pulled the rest of her shirt over her head. Her breasts were carried up then came crashing down when they were released. Her nipples stood before me again, just like at the show yesterday, and I did what came naturally. I reached up and grabbed at them, and brought my face forward to put her nipple in my mouth.

*Slap*

A sharp pain stung my face and shocked me. “I never said you could touch me,” Alex reprimanded with some authority. The surprise turned to anger in me, but was instantly mollified as she paired the slap with a hard thrust into my cock. The contrast of pain and pleasure was overwhelming and all I could do was groan and lean into the feeling. Alex pressed on with her authority by grinding her panty clad pussy into my rock hard dick and shoving her tits into my face. Knowing the consequences I had to actively resits my urge to open my mouth and take her in.

Alex turned her body so that my dick was now sliding into her ass crack, and leaned her back against my chest. With one hand reaching back to stroke my hair, she circled her hips over my groin and gave me an intoxicating overhead view of her breasts and stomach. My hands gripped the couch and all my focus was on the sensation she was giving to my dick.

Alex made little moans and bent her head back to be next to mine. “You can touch,” she whispered into my ear.

My grateful hands shot up and grabbed a hold of both tits. Alex turned her face to kiss me while I massaged her nipples. Her grinding increased in speed and one of my hands found its way down to her pussy. I massaged her through her panties. Our mouths stayed together as she groaned and exhaled into my mine. I pinched her nipple with my other hand, while sneaking a finger underneath her panties to massage her clit.

We stayed like this for a few minutes, writhing with each other and reveling in every sensation. Eventually I grabbed one of her legs and spread her out on my lap, her back still leaning on my chest, and inserted my fingers into her. Alex gasped with pleasure and pressed herself down onto me. The feeling of the wetness inside of her was incredible, and I felt along her walls until I found the ribbed g-spot. I rubbed her spot gently as I fucked her with my hand. She went wild in my lap, sitting up suddenly and putting her full weight on me while I struggled to hold onto her tits and keep my rhythm.

Alex rode my hand while groping herself and I enjoyed the view of her ass. She screamed in delight, and I was free to stroke my cock, excited by the pleasure I was giving her.

Suddenly, Alex lifted her body off my hand and whipped around. Her eyes were ravenous, and she took my hand to lick my fingers seductively. When she was done taking in her own juices, she gripped my cock and led me to the hot tub. She propped herself up on the edge and we kissed passionately as she stroked my cock. I let my hands roam all over her, pressing at times into her ass, at other times massaging her heaving breasts.

Alex turned her body and bent over the tub, looking back at me. “Fuck me.” It’s all she needed to say. I was rock hard and ready to give my cock what it had wanted for so long. From behind her I could see her perfect pussy glistening with wetness, ready for me. I lined myself up, and holding the base of my shaft, rubbed the head of my dick across her slit. Alex moaned and moved back, but I held her hips to keep her at bay. It was my turn to tease her. I gave her a slap, albeit not as hard as what she gave me before.

“Not until I say so,” I said in a call back to her control before. She smiled then closed her eyes and enjoyed my teasing as I kept my dick from penetrating fully. I played like this for a while and soaked up the site of her.

Eventually Alex couldn’t take anymore, and when she wasn’t able to thrust her ass back onto my dick, looked back at me and said, “Fuck me like you want to fuck Lily. Fuck me like your daddy fucked your sister.”

Her words struck me deep inside. I was filled with both anger and lust. I grabbed her hips, just like I had seen my father doing to Lily before, and pushed my dick as deep as I could into her. Alex screamed with pleasure and the feeling of her walls pressing down on me was intense. It was like her entire insides were trying to grip and hold onto my dick. Waves of pleasure shot through us both. To match my thrust, I felt Alex pushing her hips into me as well, begging me to go deeper. “Fuck me daddy,” she let out.

I was happy to follow this command and braced myself with her hips to give me more strength to push in and out of her. We fucked like this until we were both covered in sweat. With each of my thrusts, I watched her grateful ass take me in a jiggle. I became a little more daring and placed my thumb over her puckered asshole and massaged her lightly. I had never done this, and was pleasure when she responded with moans of pleasure.

I caught a view of us in the mirror and watched as her breasts moved back and forth. I realized I wanted them in my grasp so would have to change positions. I slowed my thrust down, and pumped for a while, making sure she was getting my full length. Slowly I pulled out and watched as her lips gripped onto my penis, then pushed in as deep as I could.

When our pace slowed, I pulled out and Alex gave me a shot of surprise and upset, as if to ask why. I took her hand and guided her to the bed. It was my turn to play on her taboo desires. “I want to fuck you where you and your dad lay.” She smiled and gave a little hop onto the bed to lay on her back. Although missionary isn’t as exciting as other positions, it gave me the best views of her breasts. Man, I loved them so much.

I spread her legs and reinserted myself into her. Alex gave a little grunt and smiled up at me. I stared down at her perfect, large breasts as they spread slightly to each side of her chest. Her nipples were a dark chocolate brown and hard as rocks. I bent myself to lick them as I started moving my hips to work her. Alex closed her eyes in ecstasy as I watched her tits bounce to my rhythm. I made sure to push myself as deep as I could get, enjoying her bodies full embrace of my 8 inches. When I bottomed out, I would push my hips deep and each time Alex let would moan, “fuuuuckkkkk” as if surprised by how good it felt. I put one hand under her and on her lower back to lift her slightly and began to pump harder. With my other hand I held her wrists above her head, stretching her body. As her tits bounced, Alex caught my eye and played to my desire. “You like watching these don’t you,” as released herself from my grip to grab her tits and helped them bounce more as I thrust in her. She gave herself pleasure and me a show my manhandling herself: pinching her nipples, squeezing her breasts, holding them both up with one arm. It was such a hot display, I could feel myself edging closer, but I knew I didn’t want to come just yet.

Sensing this, and not wanting to stop either, Alex made a move to get up and we switched positions. I lay on my back and she rode me, still giving me a view of her tits. She bounced on my dick and spun her hips in such a way that kept me edging but stopped me from cumming. I was held in a state of pure pleasure and soon she got closer and closer to her own climax. I felt the familiar feeling of her walls tightening on my dick. She began to move her hips as if she was fucking herself with my dick. I loved every second of it. The view of her body and watching her so wrapped in pleasure.

I tried to hold as much as I could, but I was close. “I’m going to cum,” I warned, to prepare her to let me pull out. But she just rode me harder.

“Don’t worry. I’m on the pill. I’m going to take all of you.” This was the hottest thing she could have said. She sped up, faster and faster; and as she did she moaned louder and louder. The pleasure in me was almost blinding as it built more intense.

Finally, I could hold it no longer, and neither could she. She let out a loud moan of pleasure and I lifted myself up to hold her and pump myself into her. I wanted to be smothered by her breasts as I came. I held her tightly and moaned a deep moan as I could feel my dick pulsing inside of her as wave after wave of cum shot into her. All thoughts vanished as I was enveloped by the pleasure. The smell and taste of sweat and lavender mixed with the warmth of our climax was almost too much to bear.

We collapsed on top of each other, and much like with my mother the day before, we did not bother to move. I loved the feeling of my dick twitching inside of her as it grew softer. The glow and warmth of sex washed over us both. I lightly caressed her back and kissed her where I could, and she seemed to purr like a kitten. The feeling of her breasts pressing into me as she lay helpless was a wonderful feeling.

When our heart rates finally returned to normal, I slipped out of her, and she lay next to me in a state of bliss.

“Thank you, I needed that,” I offered, remembering how this started.

“Mmmm, me too. Ever since the show yesterday I’d been fantasizing about getting you in me.” As she lay there, she absentmindedly stroked her own smooth skin obviously still lingering in the heightened sensual atmosphere. “Now go clean yourself up and go talk to your sister.”

“You want me to go?” This was becoming a pattern for me. I’m apparently very reluctant to leave anyone who makes me cum.

“Of course not. But you need to resolve things now that you are in a better place. Clearly your family is pretty open to not shaming desire, so there’s not a lot of downsides to talking to your sister about what you saw and how you felt.”

She had a point, but talking about it so directly would make it all real. So far, everything that had happened had felt so in the moment. I could always consciously blame being swept up in the emotions or the heat for my actions; but deep down I knew I’d have to confront that I actually wanted all of this.

I did as Alex asked and cleaned myself up. Before leaving, I kissed her deeply and we exchanged numbers. She was not someone I wanted to have been just a vacation fling.

The walk back to my room was long, partially owing to me being so relaxed and partially because I was still apprehensive of letting Lily know that I wanted more from her than a spontaneous fuck. I didn’t want this to be done when we went back to the States. As I walked, I realized that this applied to my mother too. How was I supposed to tell her that? How was this supposed to work?

As I fretted, I almost bumped into someone in front of me. “Oh, sorry.”

The woman I bumped into didn’t seem bothered and told me it was no problem. She walked away, accompanied by her young son and father, all nude of course. I thought back to what Alex told me about her dad, and what Jane mentioned about her family. Maybe, it was possible to lean in to your desires and still be a normal family.

I felt resolved by the time I reached the room door. Once I entered though, my anxiety returned. Sitting waiting for me and chatting amongst themselves was my father, mother and sister. I froze.

My mother spoke first. “Hi Jason, honey. Come here and let’s have a talk.”