Our vacation was coming to an end and Sheri was feeling a little guilty. She had got to fuck Matt and Rya next door, she had the amazing massage experience, and even an afternoon fling with Rya that we didn’t write about. While I can’t remember a time when Sheri and I had more sex over a two-week period, she was definitely afraid that I was feeling a little left out.

Sheri told me repeatedly that she had something special planned, but wouldn’t tell me any details. On our last night there, she told me that we were going out to dinner with Matt and Rya. I certainly liked Matt and Rya, and frankly, I was dying to fuck Rya, but I'd thought our last night would be ours.

In any case, I trusted Sheri and just went with it. Thank goodness I did.

The girls made reservations at a very fancy restaurant at the resort and went shopping together for new dresses. They told Matt and I to dress nicely and be ready at 6:30.

Sheri started getting ready around five. When she emerged from the bathroom, my jaw nearly hit the floor. She wore a dark purple dress that was cut so low I could almost see all her breasts. There was no way she could wear a bra in that dress and she very proudly displayed herself.

“Well, what do you think?” she asked.

“I think every waiter in the resort is going to be jacking off tonight thinking of you in the dress.”

She had hair pulled back with just a strand dangling in her face and she wore more makeup than usual, being pretty heavy on the eye makeup which she knows I like. “It’s going to be a very special night tonight,” she said as she took my hand. “I wanted to make sure that I look my best.”

I kissed her on the cheek and responded, “Well, you look absolutely amazing. I'm a very lucky man.”

We kissed for a few moments and then a knock came at the door. Sheri opened it and Matt and Rya came into our room. Sheri kissed them both on the cheek. Rya wore a tight red dress that left very little to the imagination. Much like Sheri, there was no way she was wearing underwear beneath that dress.

Rya kissed me on the cheek and whispered into my ear, “I’m really looking forward to tonight.”

“Me too. It was great getting to know you and we’ll definitely miss you after tomorrow.”

Matt had his arm around Sheri and said, “We’ll definitely keep in touch. Let’s get going, don’t want to be late for dinner.”

When we walked into the restaurant, all eyes were on the girls. They loved the attention and, I admit, I was loving the attention they were getting, too.

We drank and ate. Talked and laughed.

“Well boys, I think we’re done with dinner,” Rya said. “Why don’t we head back up to the rooms for dessert?”

Sheri looked at Rya and agreed. “I think that’s a great idea.” She looked at me and put her hand on my knee, “I know exactly what I want.”

We walked back along the path to our rooms. It was a beautiful night with a nice cool breeze. As we approached the rooms, Sheri said something to Rya. Rya then left Matt’s side and started walking with me.

She put her arm under mine so we’d walk arm and arm down the path. I put my arm around her waist instead and pulled her closer to me. I watched as Matt did the same with my wife. When we arrived back at the villas, I was prepared to say our goodnights - and goodbyes.

“I think you should come in for a drink,” Rya said and stuck her tongue in my ear. Then slid a hand down and grasped my dick through my pants, bit my ear lobe gently and said, “I promise you won’t regret it.”

Rya kissed me, letting her tongue intertwine with mine. I looked over to see Sheri kissing Matt. He looked at me with the same bewildered look on his face, so I knew he wasn’t in on the planning. This was all the girls doing.

We went into their room and the women directed us to the couch. Sheri stood in front of me and Rya in front of Matt.

Rya turned around and backed into Sheri. She grabbed Rya’s ass, reached around for her breasts and then unzipped the tight red dress. Rya had her back to us and she let the dress slink down and off her body. She stood there naked, letting Matt and I take it all in.

Rya turned and rubbed her body against Sheri, who did the same before turning her back to us while Rya unzipped her dress and let it fall to the floor. They then took turns caressing each other’s body, kissing on the mouth, and sucking nipples. Sheri was the first to reach down and put her hand on Rya’s pussy, prompting a deep sigh.

Then they stopped, turned to us and walked toward the couch. They sat between us, Sheri next to me and Rya next to Matt. They took our hands and guided us to their pussy. As we started fingering them, their hands roamed over the other woman’s body.

I slid down and started licking Sheri’s tits. She pushed on the top of my head so I’d keep going down her body. I spread her legs, dropped to my knees, and started licking her pussy.

Rya took an opposite approach. She reached down and unzipped Matt’s pants, removed his cock and leaned over to start sucking it.

Sheri was moaning loudly, but was definitely watching Rya suck Matt’s cock. After a few more moments, she pushed my head and started to stand. She grabbed my arm and motioned for me to sit on the couch next to Matt. Once I was sitting, she started blowing me, too.

Both women were standing in front of us, bent at the waist, with our throbbing dicks planted deeply in their mouths. I watched Rya slowly take Matt in and out of her mouth while Sheri did the same to me. As if it were planned, both women stopped at the same time. They stood upright and stretched briefly before kissing each other. Their tongues intertwined as their hands fondled each other’s body. 

When their kiss broke, the women begin to switch places. Bending at the waist, Rya took me into her mouth and I watched Sheri take Matt’s entire length into hers. I was mesmerized by how different Rya’s technique was from my wife’s. Her tongue swirled around my cock as it entered and exited her mouth. There wasn’t nearly as much pressure as Sheri generates when she’s blowing me, but the feeling was amazing. Looking over, I could tell Matt was enjoying the change of pace as well.

Rya continued sucking on me for a few more minutes before taking me out of her mouth. She dropped to her knees in front of me just so she could slide her entire body against mine. As she rose up, her lips momentarily touched mine. It wasn’t really a kiss as much as it was warm breath passing between us.

As her breasts reached my mouth, I felt her cunt pressed hard against my dick. She was sopping wet. Rya started to grind herself on top of me, lining herself up so I could push into her. When I did, a loud sigh escaped her lips. I’m not one to brag about such things, but I was definitely bigger than Matt. Rya could certainly tell too. She moaned as she rode me and I licked and kissed her tits.

Matt stood up from the couch and pushed Sheri to her knees. He grasped the hair on the back of her head and shoved his dick into her mouth. For a good two or three minutes, her fucked her mouth like there was no tomorrow.

Rya was going slowly and steadily up and down on my dick. She ran her fingers through my hair and cooed as I picked up the pace slightly. Being honest, it felt so good I didn’t want to change anything.

Matt sat back on the couch and I watched as Sheri straddled him like Rya was straddling me. It was easy to see the mood Sheri was in because she absolutely slammed Matt’s cock into her pussy. Sheri wanted to get fucked and wasn’t going to give Matt any option. Within seconds, Sheri was moaning loud.

Rya and I looked on while she continued riding me. Watching Sheri was turning Rya on even more and she started to go faster and a harder, too. Rya lifted her long legs off my lap and turned around to rub her ass against my dick. She bent forward enough for me to angle my cock back into her pussy. She leaned back against my chest and that’s when I started fucking her hard and fast.

As fast as we were going, I could still Sheri and Matt slapping together as they were pounding each other. Matt bit at Sheri’s nipples when she squeezed her tits together in Matt’s face. With no warning, Matt pushed Sheri off him and back onto her knees on the floor. He stood up and shoved his dick back into her mouth, fucking her like he did earlier, only faster this time.

I’ve always enjoyed watching Sheri, so the sight of her getting manhandled by Matt was a big turn on. I reached around and rubbed Rya’s clit with my fingers as I fucked her. She moaned her approval.

Taking control, Sheri then pushed Matt back so his dick was no longer down her throat. She pushed him again, this time hard enough so he sat back on the couch. Sheri then turned around and mimicked what Rya and I were doing. She lowered her pussy onto Matt’s cock and immediately started bouncing up and down on him.

Rya reached over and grabbed Sheri’s breast, pinching a nipple. The two locked eyes for a few moments as if they were savoring the feeling together.

Rya then put her hands on my legs motioning for me to stop. She lifted herself off of me and took me by the hand. She knelt down on the floor with her head between Sheri’s legs. Then she guided me to go behind her. I knelt behind her and started fucking her doggie style. Sheri grabbed Rya by the back of her head and pulled her closer. Rya’s tongue started flicking Sheri’s clit as Matt’s cock continued its assault on my wife’s cunt.

I gripped Rya’s hips and started fucking her as hard as I could possibly muster. My eyes met Sheri’s as she moaned in pure pleasure. We all continued this way for a short time and then it was time to switch again.

Sheri got off Matt, quickly kissed Rya on the mouth, then walked toward me. Matt grabbed Rya by the arm and pulled her toward him. He turned her around and had her sit on his cock like Sheri had. They instantly started fucking.

I took a very aggressive approach with Sheri. I grabbed her and bent her over the arm of the couch. She had one knee bent on the arm and her other foot firmly on the ground. I entered her from behind as she put her head on Rya’s tits. Sheri was near screaming when she decided to suck on Rya’s nipples. Rya’s head snapped back in pleasure seconds after Sheri’s tongue touched her tits. Going a step further, Sheri started rubbing Rya’s clit with her fingers. Rya was in a frenzy and Matt started fucking her even harder.

I had to slow down because I felt like I was going to cum. Sheri’s hips bucked back into me; she wanted it hard.

Just then, Matt pushed Rya off him and pulled her to the side of the couch.

Her bent her over the arm of the couch much like I had Sheri positioned. When he started fucking her again, Sheri and Rya now started kissing one another as they were face to face on the couch. Intermittently, one woman would grab the other’s breast.s

This didn’t last very long. Then Rya spoke. “I want it in my ass!” she yelled at Matt.

A grin came across Matt’s face. Instead of just pulling out of her cunt and pushing into her ass, he stopped and made her lie on the couch. He lifted her legs so her feet were up around his shoulders. He reached down and lifted her enough so he could push his cock into her ass. She yelped at the sensation, but that turned into moans as Matt steadily increased the speed.

Sheri leaned back, looked into my eyes and said, “Me too baby.”

She rolled over on the arm of the couch and got into the same position Rya was in. I lifted her legs as Matt had lifted Rya’s and pushed myself into Sheri's asshole.

As Matt and I pushed in unison, the women screamed with every thrust. Sheri licked her fingers and started rubbing her clit with all four fingers. It made me fuck her even harder. Rya reached over and grabbed at Sheri’s tits, then started rubbing and fingering her pussy as well. The two women moaned and wailed wildly. Sheri came for the first and Rya followed closely behind.

Once Rya’s orgasm had subsided, she pushed for Matt to pull out of her ass. Rya then jumped to her feet, pushed Matt down on the couch and turned so he could enter her from behind again. Matt’s cock slid deep into Rya’s pussy.

Sheri let her legs fall to my side and let my cock slide from her ass. She rose to her feet, slowly, and pushed me to sit on the couch. She knelt in front of me and played with my dick in her hands for a few moments.

“I feel so dirty,” she said and took my rod into her mouth and began an incredible blow job. Her mouth had never felt so good. Maybe it was the added fact I had just been pounding her ass or the fact that she was enjoying feeling like a dirty girl.

Rya took Sheri’s lead and decided to blow Matt again. The two women looked at each other’s eyes as our cocks disappeared into their mouths. They licked our shafts, sucked on our balls, and took our whole lengths into their mouths. After a few minutes, they switched, Rya blowing me and Sheri on Matt.

“Let’s take this to the next level,” Matt said as he motioned for Sheri to stop.

Rya took me from her mouth and stared at Matt as if she knew what was coming. Matt took Sheri by the arm, turned her around and guided her toward me on the couch. He kissed her breasts and she lowered herself onto my lap.

“Put it back in her ass,” Matt said to me.

I held Sheri around the waist and she sat on me. I pushed my dick into her asshole. I started fucking her ass and reached my hands around to hold her tits. Rya climbed on the couch next to us and started fingering herself. Her eyes were transfixed on Sheri, watching her big tits bounce up and down as I fucked her.

Then Matt used his feet to push my legs out of his way. He shoved his cock into Sheri’s cunt. We’d never tried double penetration before but, from the sounds coming out of my wife, she was certainly enjoying it.

“Oh my God, it’s so fucking good,” she yelled. “Fuck me.”

I continued rubbing and squeezing her tits and pinching her nipples. We made Sheri cum quicker than I’d ever seen her cum before. She could barely get the words out, but said, “Please... don’t... stop…fucking me! I... want... more.”

That just made Matt and I fuck her harder. Sheri screamed as if she was witnessing a murder. I could feel the pressure of Matt’s cock coursing through her as I fucked her ass harder than I ever had before. Sheri soon had her second orgasm of our DP session.

“Stop, stop, stop,” she said softly. “I need a break.”

I helped her up to her weakened legs. She sat on the couch next to Rya who kissed her cheek and breast.

Matt then grabbed Rya and shoved her onto me. She straddled me and slid my shaft into her pussy. Matt forcefully entered her ass from behind and the DP action was back on. Rya’s gorgeous, caramel breasts slapped against my face. In this position, I didn’t have to do much. Matt was fucking her so hard, she was naturally sliding up and down on my rod.

Sheri sighed in delight, her gaze locked on Rya gyrating from the two cocks filling her insides. Getting back up to her knees, Sheri leaned over and started squeezing Rya’s tits. 

Sheri started rubbing her clit again as she was getting a second wind. Matt pulled out of Rya and lifted her off me. He turned her around so I could enter her ass and he could have her pussy. We immediately started double fucking her again.

As Rya began vigorously sliding on my cock, Sheri leaned herself over and kissed my lips. Her tongue went deep into my mouth. We kissed for a few minutes while Matt and I continued to fuck his wife in both holes.

Pushing back away from me, Sheri started fingering herself and kissing Rya as Rya started to cum. Her orgasm took over her body and her juices flowed from her cunt down onto my legs.

Matt pulled Rya off of me and threw her on the couch on the opposite side of Sheri. He went to grab Sheri, but she surprised him by grabbing his dick and squeezing it hard. She started jerking him while she leaned over me to kiss me again. She changed her grip so she could get on top of me. I took one of her nipples into my mouth and I pushed my dick into her pussy. She started humping me with great force. I watched as she pulled on Matt’s cock until it was positioned at her ass. My wife wanted to get double teamed again.

Matt wasted no time and slammed himself into my gorgeous wife’s ass.

“Come on, fuck me!” Sheri said in an extremely serious voice.

We both started fucking her hard. Both us pulling almost all the way out of her then crashing back in. She squeezed her nipples in delight.

Rya, recovered from her orgasm, propped herself up on the arm of the chair to watch and played with her pussy lips and rubbed her clit.

Between getting two dicks pistoling into her, Sheri looked over and saw Rya playing with herself. She reached back and held onto Matt’s ass so he’d slow down. Then she pushed me so I’d be half lying on the couch. Sheri repositioned herself so she could lean over and reach Rya. We started fucking her again just as Sheri’s tongue reached Rya’s soaked pussy. Rya’s fingers slowly went through Sheri’s damp hair. Her mouth opened, but no sound came out as Sheri licked and lapped at her feminity.

We continued like this until Rya was moaning wildly. Sheri was about to make her cum. Matt and I slowed the pace and watched the women. Rya’s body started to shake and shift as the orgasm started. Rya gripped the back of Sheri’s head and pulled her mouth against her. Sheri made no attempt to stop.

When Rya finally came down from her high, Matt and I pulled out of Sheri just to switch things up again. Sheri and I got up from the couch and let Matt sit down. She kissed me and I could taste Rya’s juice on her lips and tongue.

Rya rolled herself down and straddle Matt once more. Sheri slowly stroked my dick and rubbed my balls with her fingers as we stood and watched.

Rya turned with her back to Matt and let him into her pussy once again. Sheri now had a taste of Rya and clearly wanted some more. She knelt down on the floor and started licking Rya’s slit as Matt’s cock slid in and out. She let her tongue slide down to Matt’s dick every few moments.

I walked over to the group on the couch and clutched my rock hard cock and shoved it into Sheri's mouth. She blew me while I was standing between Matt’s legs, who was still fucking the shit out of Rya.

Then Sheri took me from her mouth and had an evil little grin on her face. She grabbed Matt’s dick and popped it out of Rya. Sheri instantly started blowing Matt. Then she used her hand to guide my dick to Rya’s pussy.

For what seemed like hours, although I know it wasn’t, Sheri took turns sucking one cock while the other fucked Rya. Matt and I were both ready to cum, but Sheri is a master and knowing just what to do to make you hold on longer. Whoever she was sucking, she would lightly bite them, lick them, suck them with just enough force to feel amazing, but not enough to make you cum. She was and is truly amazing.

In a final move, I pulled Rya off Matt and slammed her onto the couch. I fucked her doggie style hard and fast, moving the entire couch with each thrust.

Sheri climbed on top of Matt and let him fuck her as well. She pressed her tits hard against his face.

By now the the end was near. Sheri grabbed Rya by the arm and pulled her to the floor. They knelt next to one another, kissed and rubbed each other’s tits and pussy.

Matt and I stood on either side of them and started jerking off right over their faces. The women continued enjoying each other until we were ready to make a deposit. Matt was first. Sheri turned her head toward him and helped Rya turn her body and face toward him, too. Then, the two hot women put their faces cheek-to-cheek and opened their mouths in unison, waiting for Matt’s cum.

They didn’t have to wait long. Matt fired stream after stream of thick, warm cum. He covered Sheri’s face and made sure to get some onto Rya’s tongue as well.

When he was done, the women turned to me, still pressing their faces together and opening their mouths waiting for me to fire a load. I watched Matt’s cum drip from my wife’s face onto her beautiful breasts. I shot my first stream directly into Rya’s mouth. The second sprayed Sheri on the cheek and chin and the third found her mouth. I had never cum that much in my life. Both women were cooing in enjoyment as my hot cum poured over their waiting faces.

Rya and Sheri then took turns sucking on my dick, emptying the remaining cum from my pipe.

Finally, Sheri and Rya lay on the floor, cum running all over their bodies. They kissed each other and let our cum swirl and mix between them. They kissed each other’s breasts and bodies until exhaustion took over.

Rya gave me one last kiss and Matt did the same with Sheri before they retired to their bedroom. Sheri and I fell asleep right there on the floor.

Footnote:

My wife and I have been married for fifteen years and have been together since we were sixteen year olds. We’ve grown as lovers and had a wide variety of sexual experiences. As we’ve gotten older, we’re soon to be forty, our experiences have gotten more and more intense and satisfying. Recently, we have been really turned on telling others about our stories and decided it would be fun to post a sort of history on our favorite erotic story site. There will be many, many stories written and we hope you enjoy reading them as much as we’ve enjoyed making them happen.