A Fortnight In Paradise Ch. 07

Jessica and I headed back to our hotel room, showered together (doing a bit of fooling around, but not going all the way), dressed up, and left the room. I was once again in a pair of Khaki pants but tossed on a black polo shirt, and Jessica was wearing her light blue sundress. She was definitely not wearing a bra, but I couldn't tell if she had any panties on or not.

We caught a taxi back to town and met up with Keira and Rey. Keira was in a tight-fitting, white and green striped dress, and Rey was in a dress, similar to Jessica's, but green in color.

We all three hugged each other when we met up and walked down the street to the seafood restaurant Jessica and I ate at a few days back. We enjoyed a delicious meal, sharing a bottle of wine between the four of us, and shared stories of our past. Keira having a very simple upbringing, and Rey having many stories of adventures around the world, before deciding to settle down in Nassau.

"How did you afford to travel so much," Jessica asked Rey.

"Well I kind of lived the Gypsy lifestyle. Hitched rides all over Europe, worked odd jobs here and there for cash, but never really found my calling there. I met a man while bussing tables in London, and he offered to fly me to Nassau for a weekend."

"He totally wanted to fuck you," Keira said.

"Oh, I know he did. But I wanted to fuck him, too."

"So what happened?" Jessica asked.

"We hooked up for the weekend, but he was a douche. I ended up slipping out of his hotel room while he was asleep and found a job here a couple days later. I have been here ever since."

"Wow." Jessica said.

"What about you two? I haven't heard anything about the visiting couple." Asked Keira.

"Well, Jason and I have been together for 5 years. We met during senior year of college. I had attended a frat party with my girlfriends, and once I saw him, I knew I could see myself with him."

The girls gave a simultaneous "aww" of adoration, and Jessica blushed slightly, realizing how corny she thought she sounded. I leaned over and gave her a kiss on the cheek.

After a bit more chatting and drinks, we left the restaurant and walked down the street, finding a dance club playing hip-hop music. The three girls moved towards the entrance, with me in tow. As soon as we entered, Jessica and Keira went to the dance floor, immediately pulling each other close and dancing to the beat. Rey and I headed to a nearby standing table, where we ordered drinks for the four of us, and watched the two grinding on each other.

"You are one lucky man." Rey said to me.

"I know it. Can't believe my luck." I responded.

"She is one beautiful woman, your Jessica."

"Yes. Yes, she is."

Our drinks arrived, and I signaled to Jessica if she would like hers. She nodded, grabbed Keira's hand, and the pair of them walked over to the table. Jessica came up to me, hugged me, and kissed me on the lips.

"Thank you for this trip, baby. It has been the time of my life."

"Mine too," I replied.

Jessica and Rey were the next pair to move to the dancefloor, each of them grinding on one another. I watched my beautiful woman sway her hips around, bouncing around with Rey. It was completely mesmerizing.

"I really enjoyed you inside me earlier. I would like to feel it again, "Keira said to me while watching the other two dance, "It felt so fucking good."

"Yes, it did. You have one tight pussy."

"Probably because I have never had a cock in it. I have only been with women before today, but it felt right."

"Seriously? You were a virgin?" I asked, surprised by her admittance.

"Well, I've used dildos before, but never the real thing."

"Wow. I'm honored you would choose Jessica and I to introduce you to the world of the opposite sex."

"The pleasure was all mine. Trust me." Keira stated, giving me a wink.

I smiled at her, then moved my glance back to Jessica. She was so entangled with Rey, she didn't see anything else around her.

After a few more minutes, the two of them headed back to the table. Jessica came up to me, finished off her drink, and grabbed my hand, saying "let's step outside for a minute. I need to cool down."

"Good idea, babe. Let's do it."

Jessica signaled to the other two that we were stepping out and would be right back. We walked out the front door and took a few more steps down the sidewalk.

Jessica started the conversation with, "Did you know that Keira was a virgin before today?"

"Yeah I did. She told me while you were dancing with Rey."

"Damn. I have never been with a virgin before. Except myself my first time."

"Same here."

"How was it? How did her virgin pussy feel?" Jessica asked.

"Honestly, really fucking good. She was very tight. Plus, it was the third different pussy I have felt this week, which brought more excitement to it."

"She tastes really good. So sweet."

"How are you doing, baby? You okay with all of this?"

"Oh, absolutely. Don't take me wrong, love. I love you. I am loving our vacation together. It has opened up new doors to our relationship. I am so free with you, like I never have been in the past."

"Okay baby. Just making sure. I want you to be happy, and am willing to do anything for that cause."

"Anything, you say?" Jessica said, with a devilish look in her eyes.

I look in her eyes, and say with a serious tone, "Anything."

Jessica reached her hands to my cheeks, kissed me deep, and grabbed my hand, pulling me back in the club. We walked to the dancefloor and started dancing. We felt up each other's bodies and ground into each other, reveling in the feelings.

A few minutes later, Keira and Rey joined in, dancing together next to us. Jessica motioned for them to squeeze in, and before I knew it, I had three beautiful women grinding their asses and pussies on me. We all danced together for a while, with the occasional kiss being exchanged between the ladies, and the frequent grope of each other's body parts.

We were all so horny from this, and as we left the club, Jessica and I followed Keira and Rey, both of us watching their asses sway side to side as they walked. The two ladies walked down the street, hands on each other, while Jessica and I held hands. It was clear that the two of them were horny, as their hands kept sliding to each other's asses, copping a feel.

We hailed a cab and went back to Jessica and I's hotel room. After pouring some drinks, we went out to the patio for some chatting. I pulled up the fourth chair, but Keira and Jessica immediately sat down on the same chair and started making out. Rey sat down next to me, placed her hand on my crotch, and started rubbing my cock through my khakis. I, in turn, placed my hand on Rey's inner thigh and traced a line to her pussy, and as soon as I made contact, I realized she was not wearing any panties.

"It's so freeing, having nothing on underneath. Almost rebellious." Rey said.

I slid my finger up and down her slit, spreading the juices around. Rey gave a faint moan, which caught the attention of Keira. Keira then moved her hand towards Jessica's thigh. Jessica parted her legs, giving full view of her naked pussy to all three of us. Keira slid her hand between Jessica's legs, and started rubbing her.

Jessica returned the favor, sliding her hand between Keira's thighs.

"Mmm.. Apparently, we all had the same idea. No panties night!" Jessica exclaimed.

"Well all three of us aren't wearing any underwear. Why is Jason?" Said Rey. She then moved for my pants, undid the button, and slid her hands into the waistband and started pulling down. I stood up so she could slide them down, and she did, both my pants and boxers. My cock sprang from behind the fabric, and slapped Rey in the cheek. She gave out a little giggle, then licked my cockhead and pushed me back.

"There. That's better." Rey said.

Rey stood up, turned around, and lowered herself down on top of me, pulling her dress over her head as she did so. She ground her ass on my cock, arching her back, and pressing hard. My dick started leaking some pre-cum.

Jessica was focused on Keira, with two fingers inside her pussy, and her mouth wandering down her body, spending extra time at her chest. Jessica pulled one of Keira's nipples into her mouth, bit down lightly, and sucked. This cause Keira to breathe in deep, letting a huge moan escape from between her lips. Keira leaned back in the chair, giving easier access of her pussy to Jessica. Jessica worked her way down Keira's toned stomach, tracing a path with her tongue around her heart-shaped bush, then down to her pussy lips. Keira took another big breath in, then let out another moan of pleasure.

Rey continued grinding on my cock, her ass getting covered in my pre-cum. She then slid her hips upwards, then down, causing my cock to press on the rim of her asshole.

"Do you want to fuck my ass?" Rey asked me.

"Yes, I very much do." I replied.

"Then hang on honey. Hang on for the ride."

With this, Rey spit into her hand, coated my cock, and pressed a finger into her ass to provide a bit of lube. She then lifted herself up, grabbed my cock at the base, and positioned it straight upward, lowering her body until my cockhead met her asshole. Rey took a deep breath, exhaled, then lowered herself down, sliding my cock into her ass. Rey kept sliding down until the base of my shaft was pressing against her ass cheeks.

"Oh fuck. That is so hot," Jessica said, fixated on Rey and I, "please continue."

Rey slid up and down on my cock, moving slowly at first, and working up to a nice rhythm. Meanwhile, Keira had slid down Jessica's body, with her mouth buried in my girlfriend's pussy. Keira slid one finger inside Jessica, then pulled out, moved her hand down, and slid one finger inside Jessica's ass.

"Ooh... Yeah... Oh. Oh. Ooh. Uh." Announced Jessica with each push from Keira.

"Yeah? You like that? You like my finger in your ass like that?" Keira pushed.

"Yeah. Oh, yeah. Oh, yeah. Finger my ass." Jessica moaned.

We all four continued for a while, with Jessica having an orgasm from Keira, and Rey having one while my cock was buried in her ass. After the two of them came, Rey stood up and went inside. She returned carrying something I did not expect.

"Is that a dildo? Where did you hide it?" Jessica asked.

"Oh, ha, ha. Very funny. It was in my bag. What do you say? You down?"

"Definitely. I want to see you fuck Keira with it." Jessica replied.

"Oh, please fuck me with it. I want it so bad." Keira said to Rey.

The two of them went inside, Keira laying down on the bed, Rey climbing on top, just off to the side. Rey pushed the dildo up to her mouth, pulled it inside, and covered it in saliva, then moved it down between Keira's legs. She pressed the tip to her pussy lips, then pushed harder and slid it inside. She worked Keira's pussy, sliding in and out, while Jessica and I watched from the doorway, Jessica rubbing my cock and I fingering Jessica.

Rey then pulled the dildo from Keira's pussy, flipped Keira over to her stomach, and pressed the dildo to her ass. Keira shrieked at first, clenching her body, but Rey put a hand on her back, inviting her to relax. Keira began to loosen up, and at this sign, Rey pushed the dildo in, parting Keira's ass cheeks for the first time.

Jessica and I stood back, watching, masturbating each other. What we were seeing was beyond belief. There was a beautiful brunette woman on our hotel bed, fucking a stunning blonde in the ass with a dildo. Everyone in the room was moaning in pleasure, the sights and sounds taking over us all.

Keira was the first to cum, With Rey increasing the speed of the dildo and using the other hand to reach around and finger her clit. Keira convulsed as wave after wave of pleasure flooded through her body. She kept coming and coming, and this sight brought Jessica to the verge of another orgasm.

As Keira was cumming, I sped up my movements on Jessica's pussy, sliding one finger in and out, then sliding up to her clit. Jessica then slid her own hand down to her pussy, grabbed my hand, and slid it to her side, directing me to move to the back. I obliged, and slid my hand over her ass, and then down, pressing my finger to her ass hole. I slid my finger inside, and while Jessica rubbed her pussy, she started convulsing, her ass tightening down on my finger. Jessica nearly fell to her knees, the pleasure overwhelming her. I caught her before she could fall and helped her over to the bed.

"Fuck. That was intense. I couldn't take any more at that moment." Jessica said, breathing deeply.

Keira laid on the bed, breathing deeply, slowly recovering from her recent orgasm. She then looked at Rey, then Jessica, then I, and said, "I want your cock in my ass."

"You sure? Take a minute to recover. That looked very powerful." I told her.

"I'm sure. I can take it."

"Keira, honey, his cock is bigger than this dildo. Are you sure?" Rey asked her.

"I'm sure. Get over here. Fuck my ass with your big cock."

I obliged, making sure Jessica was good before I climbed on top of Keira, lubed up my cock, and pressed it to Keira's ass. Her ass was so tight, I could only get the head in. I pulled back, which allowed Keira to loosen up, then pressed again, sliding in another inch. I repeated the motion until my whole cock was buried inside Keira's ass.

While I was working on Keira, Jessica pulled Rey down to the bed, grabbed the dildo, and began working over Rey, fingering her pussy and sliding the dildo around her asshole. Rey stuck her legs in the air, and Jessica moved on top so she could then lower her mouth down to Rey's pussy. She worked her tongue over Rey's clit, then pressed the dildo to her ass and slid it inside. Rey began moaning, which caused Keira to start moaning.

Keira began moving her hips around, positioning her body with every pump from my cock. She started convulsing again, this time harder than before.

"Keep going, Jason. Keep going," Keira announced, "I'm coming! I'm coming!"

I continued fucking Keira's ass, her muscles clenching my cock. She moaned louder and louder, and I kept pumping, giving her more and more. Keira then went limp, crossing the threshold of pleasure, and I slowed down and stopped, my cock still in her ass. Keira was breathing very heavy, unable to move. I pulled my cock from her ass and rolled to the side to make sure she was okay. She looked me in the eyes, unable to move her body, and gave me a huge smile. With this sign, I then focused on my beautiful girlfriend, watching her fuck Rey in the ass with a dildo and use her tongue on her pussy.

I decided to move down to the floor and position myself between Jessica's legs, and pressed my tongue to Jessica's pussy lips. Jessica jerked up at first, not realizing my presence, but then relaxed back down, spreading her legs more so I could dive in deeper.

Jessica remained on all fours, with myself pressing my face into her pussy, and Rey beneath her, squirming in pleasure as Jessica continued to eat her pussy and fuck her ass.

"Oh, fuck, Jess. I'm coming. Keep fucking my ass. I'm Coming!" Rey announced. Wave after wave of orgasm flowed through her body, eventually collapsing back on the bed.

Jessica stopped working on Rey, then turned her head to look at me. I had my face buried in her pussy, but Jessica had other ideas. She motioned for me to stand up, which I did, and she grabbed my cock and guided it towards her ass. I pressed, sliding my dick inside. Jessica then grabbed the dildo, wiped it on the beach towel from earlier, and pressed it into her pussy.

"Oh my god, yes. Fuck me, baby. Fuck my ass." Jessica moaned.

I continued sliding in and out of Jessica, pressure building behind my cock.

"I'm gonna cum soon, baby. Where do you want it?" I asked.

"I want it all over, baby. Shoot your cum all over us." She exclaimed.

I pulled my cock from her ass, Jessica flipped over to her back, and Keira and Rey pulled in close to Jessica. I started jerking my cock to the three beautiful women in front of me, pussies on display for me to enjoy. Jessica was still playing with her pussy and approaching her climax. She started convulsing, which sent me over the edge, and I blew my load all over them, spurt after spurt hitting them all over. My cum had hit Rey's pussy, Keira's tits, and Jessica's face. Once I gave all I had, I moved back and collapsed in the chair, my heart racing and body giving up.

Jessica moved to Rey, licking my cum off her pussy. She then moved over to Keira, licking her tits clean. Keira and Rey then moved to Jessica. Licking up and down her body until all of my cum was cleaned up.

We all sat there in silence for quite a while, absorbing the moment. Rey and Keira were cuddled up around Jessica, playing with each other's hair. I kicked back and watched, not focusing on anything in particular, but enjoying the sights before me.

After a few more minutes, I climbed into bed with the women, Jessica on one side of me, Keira and Rey on the other, and we all drifted off sleep.

Up next: Jason, Jessica, Rey and Keira head to a new island, have some fun on the open seas, then head to Rey's house for a night of pleasure.