Family Trip to Jamaica - Cover

Family Trip to Jamaica

Copyright© 2024 by Robdcruz

Chapter 4

Incest Sex Story: Chapter 4 - A mix up leads to a revealing trip for a family to a Jamaican resort. Several chapters with a slow initial build

Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa   Fa/Fa   Mult   Teenagers   Consensual   Reluctant   Heterosexual   Fiction   Sharing   Incest   Mother   Son   Brother   Sister   Father   Daughter   Group Sex   Exhibitionism   Oral Sex   Voyeurism   Nudism  

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.

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