Family Trip to Jamaica – Part 4 {Fixed}

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…..