Family Trip to Jamaica Pt. 05

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 ways...you know...she 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.

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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.

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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 across 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 married...yet," 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.