Family Trip to Jamaica- Part 5

The next morning I woke up from what seemed like the deepest and most restful sleep I've ever had. It finally happened. After so long I finally lost my virginity and my sister was the one to help make it happen. A smile crept on my face as images of Jane and Lily's cum filled mouths and writhing bodies flashed in my mind.

Last night after Jane left, we showered and cleaned each other off. Although I was exhausted from cumming over and over throughout the day, I still couldn't resist running my hands all over her body in the shower. The soap made her skin feel even more smooth, and the feeling of her soaped hand running over my cock was too much. I relented let her milk me once again. As she stroked me, we kissed passionately. I ran my hands all over her soapy tits groped at her ass. Finally, Lily got behind me and jerked me slowly. The feeling of her tits against my back and being in her control was too much and I shot my load. I couldn't believe how much I still had in the tank. Lily seemed so content, as if she lived to make me cum.

That night we had slept in separate beds, afraid mom and dad might come in through the adjoining room door and catch us in bed together in the morning. I was secretly relieved as it gave my body a chance to recuperate. I had a feeling today would be filled with even more fucking.

I looked over to the bed next door and saw Lily's fiery red hair in a mass on her pillow. She had twisted the thin blanket off her body over the course of the night, leaving her mostly exposed. She slept in a pair of men's boxers and thin white tank top. She was twisted in such a way that I could see the outlines of her pink nipples through the the thin fabric of her shirt, making me want nothing more than to reach over put them in my mouth.

Wait a minute, I thought to myself. What's stopping me? She'd probably love waking up that way.

Half-hard I started to get up when the room phone rang. Lily opened her eyes and seeing me nearly out of bed with half a hard-on made her laugh. "Answer the phone, perv."

I picked up the phone, kind of annoyed that whoever it was stopped me from getting some morning action. After a brief conversation I hung up.

"Who was it?" Lily asked.

"It was mom. She said to get up and meet them in 15 minutes downstairs in the cafe for breakfast. She said she and dad wanted to talk with us."

"Oh great. More talks about freedom and openness. I wonder what they would say if they saw how open we were last night. Ha! Dad would freak!" Lily said, laughing to herself.

"You really love teasing dad, but I have a feeling mom and dad might not be as prudish as you think. Remember mom's bikini yesterday?" Just remembering the string of her bikini passing through that firm ass made my dick twitch.

"Yea, that was pretty shocking. But come on, it's mom and dad. I had heard they had some wild days before we were born, and you can tell they are still really into each other, but still."

"Mom actually opened up when you were off frolicking on the beach. She told me about the waysyou knowshe convinces dad to open up." As I said this I realized there I was finding it more hot than embarrassing to think about what mom would look like in action.

So was Lily apparently. "Mom told you about how she gets it on with dad?That's really hot."

I was surprised, but not shocked. For one, I was feeling the same. Also, Lily and I had obviously passed the point of being squeamish about blurring family boundaries. "Honestly, I thought so too. Mom had already given me an eye full when she had me rub her down with sunscreen. Made me realize how sexy she can be." I turned to Lily to try and gauge her reaction. "You've always been close with dad. Have you ever thought about him that way?"

Lily smiled. "I guess we are way beyond hiding things aren't' we?" She moved to sit at the edge of the bed. "I think I've always wanted any attention dad would give me. When I got older, I guess I didn't separate regular attention from the attention he could give me as a man. I mean, he's still pretty hot. And from what I have seen, he's got just as nice a dick as you, little bro."

We both laughed, and I had to once again marvel at the changes we've had in a day. Here my sister and I were bonding over how fuckable our parents are. We got dressed and headed downstairs, realizing how starving we were.


We headed downstairs and walked a bit to find the dining area. I looked over at Lily to admire her choice in bikini. This one was bright yellow and looked as if a sash had been tied around her neck, with each side swooping down in about an inch of ribbon to cover her nipples, meeting again to hug her pussy and widening to cover just enough of her ass to not be considered a string bikini. Thanks to her ample ass though, it still left plenty hanging out to watch as she walked. I guess this is one of the more risque suits she referred to when we went shopping.

This morning I let Lily chose my suit, so of course she wanted me to wear what she had picked out. It was red and short, with fabric tight enough to hug my ass and gave a hint of the bulge of my dick. Not quite speedo tight tough, thank god. Lily had talked about going topless today, but we decided to see where mom and dad were at with embracing that freedom so soon.

When we walked into the dining area, I scanned the room for dad. I chuckled to myself at how quickly the shock of seeing a mass of naked bodies wears off. Not to say that I wasn't enjoying the view, but it felt much more normal. I spotted dad, shirtless, at a large table for 4 alone, a plate of eggs and fruit in front of him.

"There's dad," I said, pointing. We approached the table and dad nearly spit out his coffee when he saw Lily.

"Morning kids," he sputtered, barely registering me. "Have a seat, your mom is grabbing a bunch of food for the table."

We sat down, and sure enough Mom walked up to the table carrying a mound of food. It was my turn to spit out my drink. As she bent to place the food onto the table she treated all of us with a view of her incredible breasts. Perfect little mounds, looking bigger still because of her slender yet fit frame. Her nipples small points of pink on perfectly round, quarter sized areolas. Hugging her firm ass was the bottom half of the same type of string bikini she wore yesterday, but this time in blue.

"Hope you kids are hungry." Starved, I thought. In so many ways.

"Wow mom, you're really putting it all out there. Very brave," Lily said.

"Not all," mom laughed as she patted the front of her bikini bottoms. "Not yet at least. We told you kids that your father and I would probably be taking part in the freedoms this resort allows. And you both are free to as well."

Lily and I both looked over to dad, expecting him to be stressed, but he was calm and smiling. Lily asked, "This really OK with you, dad?"

"Yes, sweetie. I think this could be good for us as a family. Being brave and trying something new. How about you kids?"

I was still staring at mom, but managed to get out, "Yea sure. If it's OK with you guys."

"I think it's great," said Lily, giving a smile to both mom and dad. Under the table I felt her hand give my dick a quick grab. I couldn't tell if it was because she was horny for me, or excited for these changes in our family.

The rest of breakfast passed by uneventfully. It was actually nice how relaxed everyone seemed. Despite that, I made sure to take in the view of mom's body as much as possible. Mom and I decided to hit the beach (I was hoping I'd find the girl I'd been oggling yesterday again). Lily and dad were going to try out the resort spa. They were always the one's in the family to jump at the chance to be pampered. With breakfast done, we split up.


Lily and Dad

Dad and I made our way to the resort spa, which was set at the far end of the resort. Through the large glass double doors was the typical calm space you would expect. A water feature ran down one wall into a small pool, making gentle trickling sounds, while soothing music played in the background. We gave our room numbers to the male attendant behind the counter to charge and I gave a little peak to confirm that he was fully nude. He caught my eye and smiled.

"The lounge where you can disrobe is to the right. Through there are the doors to the spa where you are free to enjoy whatever ammenities you wish," he informed us.

We made our way into the lounge. In the corner, two older women were sitting nude enjoying refreshing cucumber water and chatting. Their skin a bright pink, either from the beach or the sauna.

"Dry or wet?" My dad asked with a smirk.

I laughed, thinking how odd that sounded. We always started off in the saunas. "Let's get a good sweat going in the dry." We entered our changing rooms, and I stripped off my tiny bathing suit. I wondered what dad had thought of it, hoping he had been enjoying the views. I donned the light, cotton robe, and enjoyed the smooth feeling as it rubbed against my bare skin. I wrapped a towel around my waist and exited the stall to find dad already waiting with his towel. From its tightness, I tried to discern whether a bulge could be seen, but the thick towel fabric made it difficult.

We opened the door to the dry sauna and I was hit with the amazing sensation of intense dry heat and the smell of wood you always get in these rooms. As dad entered, I took a deep breath and stripped my robe off, placing it on a hook at the door. Dad had found a seat at an elevated corner bench, and looked up as he sat down. His eyes grew big and I watched him look from my face to my tits, then look away again. His legs shifted uncomfortably, and I wondered if he was trying to hide a growing erection.

"Is this OK, daddy?" I asked, realizing as I said it how intentionally I used the word 'daddy.'

"Yes, of course, honey. As long as you are comfortable." And with that he leaned back, resting on his elbows and tried his best to stare at the ceiling.

I sat close, but catty-corner to him on a lower bench. Again, summoning my bravery, I leaned back in the same way my father had, leaving my breasts fully on display. I closed my eyes and imagined my dad stealing glancing and maybe even touching himself.

The feeling of the sweat pouring down my body was relaxing, yet also arousing. I especially enjoyed feeling of a cold bead of sweat trickling down the space between my breasts. I reached up involuntarily to wipe the sweat and caused my breasts to jiggle. Looking down, I had to appreciate what a body I had been blessed with. My stomach was flat but didn't make me look skinny, and you could just make out my hips flaring out to meet my healthy ass at the top of my towel. I loved my pale skin, and the way it made my red hair stand out even more.

I looked over to dad, who had remained with his eyes closed. I gave an internal gasp as I realized he must have relaxed enough to not realize that from my vantage point I could see right up his towel. Hanging between his legs, was a soft but incredibly thick penis. I could barely contain myself, thinking of wrapping my lips around it. I wondered if his cum tasted like Jason's. Suddenly, I saw it twitch, and I looked up at dad who was looking right me. He closed his legs and shifted, blocking my view.

"Everything OK, Lily?" I could tell he didn't really know what to say.

"Yea, dad. Just taking in the view," I joked.

This actually made him laugh. I looked over across the room and saw a man and a woman, without even a towel, sitting accros the large sauna. They both glistened with sweat. The man was gently rubbing her clit while the woman stroked him slowly, almost lazily. Dad followed my gaze, and we both sat for a while watching the couple enjoy each other. The woman eventually looked up to meet our stares and smiled.

Looking over to my dad, I saw his towel tenting. I decided to give him a break for once. "I think I've had my fill though. Should we move on?"

"Umm, sure sweetie. How about a cold shower?"

I laughed, thinking about how both of us could use some cold water to calm down the sexual tension. I led the way, and as we exited the sauna we were met by the front desk clerk.

"I hope you enjoyed the sauna. You certainly worked up a sweat," he said looking over our glistening bodies. "A spot for a massage just opened up and I was wondering if you two would be interested. It would be with our compliments of course."

How perfect. I loved massages and I know my dad did as well. Back home we would try to go at least once a month. "That sounds lovely. Thank you."

"That's wonderful. I am sure you would like to shower off. The showers are right over there, and when you and your husband are ready, you can enter the parlor through that door for your couples massage."

"She's not my" My dad began to interject.

"We aren't marriedyet," I said quickly. "But through those doors? Thank you." I took my father's hand and began to walk to the showers.

"Lily, what the hell?"

"It's a free massage dad. I mean come one. Why give that up just because he made a mistake and thought we were together?" I knew we had the money to pay for whatever massage we wanted, so I added, "besides, things are always more fun when they are free."

Dad could tell I was insistent so he just shrugged. We made our way to the showers, which was just an open, tiled room, with shower heads lining three walls. Dad looked around for a stall or another room, but it was obvious that this was it.

"Umm, well I guess I'll take this wall and you take that one," he said, gesturing to the opposite wall. "I promise I won't look, sweetie."

"Right back at ya," I said awkwardly. Right back at ya? What the hell was that? The tension between our normal sense of privacy and my growing desire to see my dad naked was making me lose my cool.

We walked to opposite ends, and I placed my towel on a hook. I could hear my dad start his shower, and I started mine. As the cool water hit my skin and washed my sweat away, I realized how sexy it was to think that we were both completely nude in the same shower. I imagining him running his hands over his body and over his thick penis. I hoped he would be stealing glances back at me. With that in mind I ran my hands seductively over my own body. I enjoyed running my hands over my ass to wipe the sweat away and groping my thickness. I bent down and stuck my ass out as I ran my hands down my legs. I wanted so badly to touch my pulsing pussy thinking about my dad watching this from the other side.

Soon, I heard his shower turn off and he said "OK honey. Let me know when you have your towel on again, so we can head to the massage."

I grabbed my towel and gave myself a quick pat down before wrapping it around my waist. "Ok, ready." I turned to see my dad with his towel on. From the front of the towel I could clearly see a straining dick trying to break free. My dad held the towel in the front, attempting to hide it. I felt my cheeks blush a bit knowing he must have been watching me.

We made our way through another set of doors to a dimly lit hallway. There at one door stood a tall, nude Jamaican woman with dark skin, curly long hair, a slim but solidly fit body, and large beautiful breasts. As she ushered us into the room she turned and I could see she was blessed with an ass similar to my mother's in its firmness, but a bit bigger. Maybe just an assumption because she's a masseuse, but I she must keep fit and slender through yoga.

I was so busy soaking up the beautiful woman that I almost missed my dad's reaction. He too was admiring her and a pit of jealousy sat in my stomach. It was a similar jealousy I had felt when I watched Jane take in Jason's cum last night. Apparently I was a very possessive young woman. Seeing my dad lust for another made me want to push her aside and grab his cock for myself. But I pushed that thought aside and entered the room.

The room was as dimly lit as the hallway and accented with soft, ambient red lighting. In the center of the room was a massage bed.

"My name is Brianna and I'll be your masseuse today. Before we get started, you can both place your towels on the bench over there." She gestured to the corner of the room.

I guess I knew this moment was coming. I didn't want to show any hesitation fearing it would scare dad off from the whole experience. I confidently walked to the bench and dropped my towel. I turned to my father, completely nude. The room was dark enough that he was more in shadow than in light, and I assumed he saw the same with me as well. I could tell that seeing me nude in this light was still a lot for him, but to my surprise, Dad walked up and placed his towel on the bench next to mine. We stood facing each other, looking over one another's body silently. I could see his strong arms, and further down his thick cock was growing ever so slightly. I could see him drink in the sight of my breast, hard nipples, and red trimmed hair above my young pussy. The shadows gave everything such an erotic tension, I was thankful when Brianna spoke up.

"So who would like to give the massage?"

We both looked at her dumbfounded. "Give the massage? Ummm. I assume that would be you, right Brianna?" I said.

"Well, in a manner of speaking yes, my dear. Maybe it was unclear. This is a sensual massage class for couples. I will guide you both in the art of using touch to excite your partner while prolonging pleasure without orgasm. I'll be here only to give hands on help and stop things from going too, far too fast." Brianna spoke in such a professional and convincing manner, it felt like the most natural thing in the world.

I knew that my dad and I were past the point of no return from the moment we looked each other over in the nude. We would go with whatever the resort could bring us.

"I'll give the massage," I offered. I wanted the control in the situation. I wanted to guarantee, that if I desired, I could grab my father's cock and do with it whatever I chose. And with that, Brianna guided my father, who gave me a small, tender smile, to the table and had him lay face down. I chuckled when it became obvious he would have to physically adjust his penis before he could lay flat.

Brianna then guided me to my father's side. Looking down I could see his strong back, and nice, firm ass. "First, we will rub your partner with oils. He'll feel a warm sensation that will radiate as if just below the skin." She poured a thick oil into her long, slender hands, then clasped mine to to spread the oil into mine. Indeed it felt pleasantly warm. Brianna then guided my hands onto my fathers back, and had me massage him starting from the shoulders. As she guided me, I could feel her large breasts push against my bare back, and one of her legs moved to the outside of mine. She was so tall she hovered over me, and her breasts threatened to pop over my shoulder. I enjoyed the contrast between the softness of her breasts with the hard muscle of my father.

I brought my attention to my father's back and felt the tense muscles underneath. Brianna guided the pressure, pushing down periodically as we moved lower. She moved me to the brink of his ass, and I watched my father tense slightly in anticipation. But Briana moved me back up his back to his neck.

"The goal of a sensual massage is to connect with your partner and bring them pleasure, without pushing them over the edge. Don't be afraid to gently tease your partner's expectation." We massaged my fathers neck, and I felt him relax a great deal. It was so arousing to know that I was giving him this pleasure.

"Press your body into your partner's. Let them feel your curves as you move across the body." And with that, Brianna gently guided me to lower my body so that as we moved down my father's back, my nipple grazed his skin. My father and I both let out a gasp of excitement. For him, I imagined the press of my tits excited him as he has been lusting over them for years. For me, that same excitement was double because of the sensation of the warm oil on my sensitive nipple.

Finally, we massaged my father's ass and Brianna guided me to not only massage him deeply, but to tease my father by moving my hands into his upper thigh and up, almost touching his balls. My father spread his legs a bit, hoping - begging - to be fondled. Brianna moved my hands so that we both made contact and gentle brushed against my father's testicles. I watched him pushed himself into the table and he let out of a moan of pleasure.

Our hands then moved away, and massaged down to his feet. Brianna then tapped my dad's leg and asked him to flip over. I was so turned on and couldn't wait to see the effect I had on my father. He hesitated, then shifted himself to flip over. His cock sprung up and stood straight up in attention. It was similar to Jason's, but much thicker. My dad looked me in the eyes, willing me to be OK. I looked back and smiled to assure him. Such intense desire welled up in me. I wanted to bad to feel his cock. To stroke it. To suck it. I wanted to look up and see my dad's eyes watching me approvingly as I took him all in.

"Your partner is showing you how aroused you have made him, and it is OK to show him the same." Brianna reached from behind me, down across my front with her long arm, brushing my breast, and slid her slender fingers across my soaking slit. A wave of pleasure shot through me, and I let out a moan while grasping her arm. Brianna reached with her now soaking finger, and circled the tip of my father's dick with my juices. My dad arched his head back and bucked his hips up. It was as if his penis was aching to be firmly stroked or fucked. "Now you try," Brianna urged me.

Almost in a trance, I looked my father in the eyes as I reached down to my mound. He followed my hand with his eyes, and watched as I, unable to resist, inserted my finger into my waiting hole. Brianna's hand was quick to envelope mine and pull me out.

"Now, now. the goal is to excite, not to cum." I flashed with frustration that turned to something else. There was a part in me that wanted to throw Brianna down and ravage her body. I wanted to fight and fuck her. Her control and guidance were so smooth it aroused me to no end. She guided my hand, wet with my own cum, to my father's waiting cock. She held my finger out and slowly traced his tip, careful not to apply too much pressure in any one spot.

My god, I thought. I'm touching my father's penis. It's so big and smooth. I wanted nothing more than to take it in me. I thought I heard my father give a whimper as he edged with a desire for release. Brianna intruded on my thoughts, "I can see both our lovers are growing impatient and can't take anymore. The sexual tension between you is intense. With practice, you will be able to stay in this tension for longer periods of time. Let's move on to something new. "

Brianna helped my father up and guided both of us to sit on what looked like a large yoga mat on the floor. My father and I were completely in her hands. I realized that letting her take over almost completely relieved me of needing to feel guilty about my desire for my father. She sat us down across from and facing each other, legs extended so that his were over mine, and my feet rested just around his ass. His rock hard dick sat directly in front of my soaking wet pussy. They were so close I imagined I could feel its warmth.

Brianna placed our arms on each other's shoulders. "Under no circumstances are you to touch each others genitals. This exercise will allow you to maintain your arousal while also letting things cool enough to avoid climax. Look deeply into your partner's eyes. You will now say their name, and what you want them to do to you. Sir, you will begin."

"Lily, I want so badly for you to reach down and grab my cock. I want to feel your hand grip it and put it wherever you want." Hearing him speak so clearly of his desire sent a ripple of pleasure through me that settled into my stomach. I yearned to reach out, but knew I could not.

"Now you, Lily," Brianna encouraged.

"Da---John," oops. Out of the corner of my eye, I could see Brianna's head turn slightly with interest. I pressed on. "I want you to bend me over and push yourself deep into me. I want to feel your thickness filling me up." Dad's prick twitched as if to try to grant my request.

"Good. Now hold that pose while I ready the Nuru gel."

I was so curious as to what was next, but at the same time could not stop looking into my father's eyes. I could feel his desire. I knew instantly that he had wanted this for a long time. I hoped he knew that this was my secret desire as well.

Brianna returned with a large basin of clear gel. "This is a special massage gel from Japan. I will spread this over your bodies, and guide you in its use. Lily you will slide over John, using your body to massage and stimulate him. There is to be no penetration at this stage." She then dipped her hand in the gel, and began to spread it over my shoulders, over my back, across my legs, and finally over my breasts. Her expert hands massaged my breasts and gently teased my nipples. Her body pressed against mine as she spread the gel, making her black skin glisten and catch the little light in the room. The gel felt cool and soothing. It dripped down to my pussy and she spread it across the lips, then moved back to spread it over my ass.

With a sloppy, gel soaked hand, she laid my father back so he was lying flat. She spread the gel over his chest and legs, leaving his penis dry. "Lily will get that," she said with a wink.

She directed me to sit on his legs, and slid me up. I was surprised at how smoothly I moved up my father's body. The gel created such a smooth surface on both our skins there was barely any resistance. I realized what was about to happen before my father. He had put his head back, and was enjoying the sensation. With Brianna's guidance, my sopping wet and lubricated pussy rolled over and flattened his waiting hard cock. Its stiffness moved through my slit and threatened to enter. I yelped with pleasure and my father's hands lifted to grip my hips. Again, Brianna was quick with her own hands, and held my father down.

My body took over, no longer needing Brianna's guidance. I slipped my pussy over my father's body, occasionally returning to his cock to tease it. I used my hips to rock myself into him. My father each time tried to hold me in place over his cock, but was held firm in place by Brianna. I laid flat, letting my slippery breasts spread the gel over him as well.

We both moaned with each pass of pleasure. I reversed and gave my father a view of my ass. He was confronted by my large, shining pale globes and was allowed to roam his hands over them by Brianna. I reached back and pressed his dick up against my ass, moving my body up and down, rubbing it on the crack but stopping it from making purchase inside me. I was so horny and free I had the thought to let him into my asshole, imagining that it would slide in easily, without pain. But I didn't dare.

After what seemed like an eternity of pleasure, Brianna, herself now completely shining with gel, said, "Now is the moment your bodies have been preparing for. It's time you embraced and be joined together."

And with my father still laying on his back, Brianna helped me up, guiding me over his waiting cock. My dad stabbed himself into me and the pleasure was unlike anything I had ever experienced. As I wished, daddy filled me up completely. We both screamed in pleasure.

Out of the corner of my eye, I could see Brianna leaning against the massage table, apparently herself unable to resist. She was spread, the pinkness of her pussy a stark contrast to her dark black skin. She fingered herself vigorously, while clutching her breast. While dad fucked me, I could not resist and reached my hand out to her. She had been so a part of this and had commanded me so much, I needed to taste her. Knowing what I wanted, doubtlessly having been in this situation many times before, she took my hand and stood over me, offering me her pussy to eat. She was tall enough that I barely had to extend myself to lap at her.

I felt my father's hand grope by breasts and pinch my nipples as he grunted. I released myself from Brianna's wetness and screamed "harder!" to my father. Wanting him to pound himself into me. I retuned to Brianna and sucked her clit and rammed my tongue into her. My father listened well, and pounded my tiny vagina as hard as he could.

My father was the first to go. I felt him push deep into me and explode with what felt like gallons of cum. This was the prize of all the teasing and waiting. He continued to fuck me while filling me, pushing me over the edge as well. My pussy gripped his dick and I was enveloped with a full body sensation. I moaned deeply as I felt myself melting away. Like dominos falling one after another, Brianna was next. With a yell, she came hard and I could feel her wetness surge down my chin and I weakly lapped at her.

Brianna moved to lean on the table again, as if to give my father and I some space. I collapsed on top of him while he was still in me. There was no way I was going to move. I wanted to feel him inside me forever.

"Oh baby," my father uttered and put his arms over my back. I could feel his softening dick twitching inside me, as his cum flowed out of me.

I pushed my body and breasts into his chest, still slippery from the nuru gel.

"Mmmm. Thank you daddy," was all I could reply.

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