During week one of the holiday, Mikki and I had fun with four new male friends, walked naked on a nudist beach, and flashed our tits when ever we could. I became a member of the mile high club, Mikki and I had both experienced two Spanish cocks. Whilst Bobbie and James were on an excursion, Mikki and I had fun with two bartenders, letting them both fuck us. We were both hand spanked for our mischievous behaviour. Week two sees us both having more fun with more cock and a new pussy.
That night, we went out to a bar in the main town, enjoying drinks and dancing in a lively, crowded venue. A couple our age asked if they could join us since there were no free tables. We got along well as we exchanged stories about our lives. They were Luke and Sarah, both twenty-three, married for two years, and on their first holiday since their honeymoon.
We shared our own story, prompting Sarah to express sympathy about Mikki’s first marriage, though Mikki explained that everything had worked out well and that James was much kinder. Sarah was surprised to learn that the four of us were sharing a room and said she wanted more details the following day. We all walked back together; as we parted ways, Sarah invited us to join them at their hotel's pool in the morning, and we agreed to meet at ten.
After breakfast, we put on our bikini wraps, grabbed towels and sunscreen, and set off. The hotel featured a children’s pool as well as a spacious adult pool with bridges and a central bar. Everything was very pleasant, though the only drawback was that while sun loungers allowed topless tanning, you had to be covered when walking around, swimming, or at the bar.
After lunch, we invited our new friends to our pool and explained that there was a separate adult area where topless bathing was allowed. Sarah appreciated that since she was eager to tan her white bits. Back at the pool, I noticed James and Bobbie casting sly glances at Sarah’s breasts while Luke eyed both mine and Mikki’s.
It was a fun afternoon that allowed us all to get to know each other better, and we agreed to meet again after dinner at the same bar from the night before.
We started the evening with a drink and a dance, but the noise made conversation nearly impossible, so we moved to a quieter bar. While the guys headed off to play pool, the three of us women began chatting. Sarah was extremely curious about our living situation. We explained the background of our unexpected arrangement: the accidental swap at a party, having Mikki move in and share our bed, how she met James, started dating him, then he eventually moved in, and now all of us live and sleep together. We also mentioned the list and shared some of the challenges we’d undertaken, including those during this very holiday.
Sarah kept peppering us with questions—it was obvious her curiosity went beyond mere interest. Later, she invited us to their room for a drink. Although their room had a generous balcony, it lacked the intimacy of ours. As we said our goodbyes, Sarah mentioned she’d see us at our pool at ten.
The following day, we all spent time together by the pool, enjoying lunch topless. Sarah commented on how liberating it felt to be free while sitting and eating outdoors. After a few drinks, we returned to the pool, while the guys announced they were off to the beach to swim in the sea. Sarah then nervously confided that she and Luke had discussed our unique living arrangement and admitted that they often entertained the idea of experimenting with others.
Mikki and I offered her some advice on exploring new experiences, stressing that clear communication and honesty were essential. Sarah then asked if she could join us one evening to see how things unfolded. I assured her that after dinner we would head to our room, take things slowly, and see what happened—emphasizing that everyone could speak up if anything felt off and that no one would be pressured into anything they weren’t comfortable with.
That night, we all went to a restaurant we’d been eager to try. After a pleasant meal and a couple of bottles of wine, we enjoyed cocktails at our pool bar and relaxed. I leaned close to Sarah and whispered, “Are you alright?” to which she replied softly, nervous yet assured. I took her hand; noticing this, Mikki took Luke’s, and soon we all made our way back to our room, with Bobbie and James trailing behind.
Sarah was clearly impressed with the room—with its two large beds and private balcony. Once inside, we uncorked a bottle of wine, and Bobbie retrieved a deck of cards. We filled shot glasses and poured wine as we agreed on a game: the loser of each round would remove an item of clothing and take a shot, all designed to break the ice.
Before long, we were down to our underwear. Sarah was the first to lose her bra, and Mikki ended up being the first completely naked, much to Luke’s delight. One of the guys then lost a round and had to remove his underwear, his growing arousal on display.
Mikki then initiated a series of dares. First, the guys began kissing and caressing our breasts. Next, Mikki was challenged to stroke Luke’s aroused cock, which was already fully hard. Watching Sarah smile, she leaned over and gave it a few delicate strokes, drawing a soft moan from Luke. It seemed Mikki had arranged the game, because the next dare had Sarah stroking James’s erection. Then it came to me: I was dared to give Luke a two-minute blowjob. I checked in with Sarah; with her nod of reassurance, I knelt before Luke, took him in hand, and gradually lowered my mouth until I had taken him more deeply, eventually working him carefully until I had his full length in my throat. I was lost in the moment when Mikki suddenly called, “Time!”
After the remaining articles of clothing were shed, the guys lined up, and the three of us each knelt before a partner—Sarah with Bobbie, Mikki with Luke, and me with James. We all sucked their cocks, each of us bringing them to full arousal.
Later, Bobbie took Sarah to one of the beds, I led James to the other. Meanwhile, Mikki accompanied Luke to the settee, and kisses were exchanged among us. At one point, Mikki pulled Sarah aside and mentioned that Luke felt a bit uneasy with all of us together. She proposed taking him to his room for the night if he was more comfortable that way, and if Sarah was agreeable, she could spend the night here. Sarah agreed, admitting she too felt somewhat self-conscious.
Mikki and Luke then dressed and, before departing, Mikki kissed both Sarah and me, urging us to have fun. Once they left, Sarah relaxed further and began to enjoy the night. I suggested to James that he join them while I watched. James positioned Sarah on all fours, slowly rubbing his cock against her pussy, eliciting soft moans as he entered her. Bobbie then brought his cock to her mouth, and without hesitation, she welcomed him completely.
I lay back, fingers teasing myself, as the guys swapped places. Bobbie slid into Sarah’s pussy and I felt a rush of excitement. I’d watched him fuck Mikki and Katy before and always loved seeing his first time with someone new. It struck me I’d had far more cocks than he had pussy’s since our wedding, so I mentally noted I’d need to remedy that when we got home.
Bobbie and Sarah found a steady rhythm while Sarah worked James’s cock in her mouth beside them. Hearing her moans grow more urgent, I stroked my clit faster and thrust my fingers deep, aiming to climax in sync with her. As Sarah cried out that she was about to come, I pressed harder—and we both exploded together, her body rocking on Bobbie’s hard thrusts.
Our breathing heavy, Bobbie eased up, pumping slowly as James’s cock slipped free of Sarah’s mouth. Once she’d calmed down, she wrapped her lips around him again and stroked with her hand. Soon James warned he was close; she held him in her mouth until he released, swallowing every drop.
Moments later Bobbie asked if he could cum inside her. Sarah nodded, urging him not to pull out but to fill her. With a final deep thrust, he emptied himself into her. Pulling out, they both dripped with his cum, and I leaned forward to clean him with eager licks.
Then I turned to Sarah, lowering my head between her thighs to taste the spilled cum. She tensed at first, but when I sucked her clit and licked gently, she relaxed and melted into it. Just as I neared my own orgasm, she gripped my hair, pressing me harder until she cried out again, body stiffening and spasming around my tongue.
When she finally released me, she whispered, “Thank you—that was my first time.”
I climbed into bed beside Bobbie while Sarah and James shared the other bed. We all made slow, lingering love until each of us came again. “That was fun,” I said. Sarah smiled in agreement.
Later, we drifted off. In the morning, I headed for a shower; James joined me and we washed each other, then towelled off. As we walked back toward the bedroom, we heard Sarah chatting with Bobbie over the sound of her own shower.
After we had towelled off, Mikki returned grinning ear to ear, clearly having enjoyed her night. I pulled Sarah aside and suggested she spend the day alone with Luke to discuss everything and ensure they were both content. I told her we'd head to the beach and meet them for drinks at our bar come dinner time.
We agreed to spend another day at the nudist beach. While we didn't catch anyone putting on a show in the dunes, we still had a great time.
Post-shower and change, we went to the bar, where I again took Sarah aside to check in. She said they'd both shared their concerns but were overall happy with what had happened. She mentioned they wanted to try it again, this time together, to watch each other with different partners. We agreed that after dinner, we'd all go to our room, and each of the three women would get to try three different partners.
Back in the room, there was no need for games; everyone simply undressed and paired up. I suggested the three women get on their hands and knees at the edge of the bed, with a partner behind them. Sarah paired with James, I with Luke, and Mikki with Bobbie. Every five minutes, the guys would move down one until the last guy finished.
The three men positioned themselves and began, moving down one spot each time the timer went off. We'd all had three partners twice when Luke announced he was coming in me. I pushed back to take his cum, then Bobbie came in Sarah, and finally, she got a second load from James. Mikki went straight down to clean her up.
In the next game, the guys lay back on the bed while the women sucked their cocks for five minutes before moving on. They kept switching until all three guys had come. This was a lot of fun; Luke was again the first to come, this time in Mikki's mouth. I took Bobbie's, then Sarah got a load from James.
Afterward, we all sat naked on the balcony, drinking wine, and chatting about how much fun we'd had. Sarah and Luke said they were going back to their room for some alone time. After getting dressed, they thanked us, and we agreed to meet up at ten at our pool.
After a late breakfast, we meet up with Sarah and Luke at the pool. After about thirty minutes, Sarah suggests we grab some drinks. While we're waiting for them, Sarah shares that she has loved everything that has happened so far. She mentions how she and Luke are thrilled with the fun they've had and plan to continue once they're back home. They even have a few couples in mind who might be interested in joining in. Luke mentions he knows some guys who are attracted to Sarah, and they might be keen on a threesome, which Sarah is open to.
Sarah then leans in and whispers there's one thing she'd like to try before we leave. Curious, I ask what it is. She admits she enjoyed when Mikki and I went down on her and would like to try it herself, but feels too shy to do so in front of Luke and the other guys. I assure her that it would be fun and promise to arrange something for later.
We return with the drinks and distribute them. When I got a moment, I quietly asked Bobbie if he could take the guys for a walk and a drink in the afternoon. Smiling, he inquires about my plan, so I explain that Sarah wants to experiment but feels nervous with the guys around. He assures me he’ll handle it. I thank him with a hug and a kiss. We’d had a light lunch when Bobbie announced that he and the guys were going for a walk and a few beers. Once they’d left, the three of us headed to our room, uncorked a bottle of wine, filled our glasses getting a bottle of water, and stripped off. Naked, we settled on the balcony, staring out at the sea. It was our last night here before flying home tomorrow evening.
At first we chatted about nothing in particular, until the conversation turned to sex. Sarah was still fascinated by our living and sleeping arrangements, and Mikki reminded her that in our little group, everyone was free to be intimate with whoever we wanted, whenever we wanted—no jealousy, no rivalry. I confessed that all this talk was turning me on, and suggested we head to the bedroom.
On the bed, I took Sarah’s hand and told her that if she ever felt uncomfortable, she only had to say so, and we’d stop. Mikki wasted no time: she eased Sarah onto her back and began kissing her deeply. I moved in to stroke Sarah’s breasts, pinching her nipples until she moaned with pleasure. Mikki trailed kisses down Sarah’s body, and I kissed her lush, soft lips. Then Mikki parted Sarah’s knees, kissed along her slit, and gently took her clitoris into her mouth. Sarah’s moans pressed against me as I kissed her again.
Mikki licked and inserted a finger; Sarah’s moans grew louder. I tapped Mikki on the shoulder for my turn. As I licked and kissed Sarah’s pussy, Mikki focused on her breasts. I slid two fingers in and out of her, nibbling her clit. Sarah began to buck against me, her hands gathering at my hair to pull me closer. With a sharp cry, she came, her release splashing across my face. I tenderly licked her clean as she trembled through the last waves of pleasure.
When Sarah had recovered, she thanked us for the incredible climax—then announced it was Mikki’s turn. I moved to the edge of the other bed, letting them have space. Sarah kissed every inch of Mikki’s breasts, caressed her nipples, then worked her way down to Mikki’s pussy. Cautiously at first, Sarah flicked out her tongue; soon she was moaning as her pace grew more confident. Mikki told her to slip in a finger, then another. When Sarah’s tongue and fingers found their rhythm, Mikki shuddered and climaxed with loud gasps and tremors.
Mikki rewarded Sarah with a long kiss, praising her. I asked Sarah how it felt; she said that it was even better than she’d imagined. Then she looked at me and said, “Your turn.” I swapped places with Mikki, and Sarah expertly slid between my legs. She was a quick study—before I knew it, she had me on the edge, and I gave in to a fierce, sudden climax that left me breathless.
After a quick freshen-up, we returned naked to the balcony with more wine and water. On the second glass, I suggested trying something a friend had once told me about. As long as it involved no pain, they were in. Back in the bedroom, I spread a blanket on the floor. I had Mikki lie on her side facing inward, then Sarah on her side with her head between Mikki’s legs. I parted their feet and lay down so my head was between Sarah’s legs. Finally, Mikki turned her head to rest between my thighs. In our little triangle, each of us could lick a different pussy while another licked ours.
It felt awkward at first, but we quickly found the groove. Sarah was first to cum, followed by me, and then Mikki. Lying back to catch our breath, we laughed when Mikki said, “Why wasn’t this on our challenge list?” After freshening up in the shower, we returned to the balcony to wait nude for the guys.
When they came back, they seemed surprised to find three naked, very aroused women lounging on the balcony. Sarah grabbed my hand and led me to the bed. “Watch this,” she said with a grin, and we slid into a sixty-nine, tongues exploring each other’s pussies. The look on Luke’s face was priceless. Soon the guys were stripping off, visibly hardening.
We three sat side by side, each taking a cock in our mouths. Sarah called “swap,” and the guys rotated. Then Mikki called “swap,” and they rotated again, all three men rock-hard. Finally, we paired off with our own partners: Bobbie with me on one bed, the other four on the second bed. Without any more foreplay, the guys fucked us hard in missionary until every last one of us came.
As we lay spent, Luke said it was the most erotic thing he’d ever seen. Sarah snuggled next to him, kissed his cheek, and thanked him for joining us, promising him plenty more pussy in the future. Luke just smiled and replied, “And I’ll watch you getting fucked by all your friends.” We burst out laughing—so much had changed since our first drink together.
Sarah and Luke returned to their hotel. We agreed to meet them outside at eight for dinner on our final evening here.
After changing into summer dresses and sexy lingerie, we headed to their hotel and chose a seafood restaurant right on the beach. The meal was delicious and the wine flowed freely; by ten-thirty, we’d all had enough. While we were splitting the bill, I leaned toward Bobbie and asked if he’d mind if I spent the night in Luke’s room. He kissed me, told me to enjoy myself, and joked that the rest of them would surely find ways to keep busy.
Next, I checked in with Sarah. She grinned and said, “Great—another night with Bobbie and James’s hard cocks, not to mention Mikki’s juicy pussy.” Back at the hotel, I took Luke’s hand and led him to the front door, where he looked pleasantly surprised. We waved goodbye to the others and slipped into his bedroom.
Mikki had raved about her solo night with Luke and insisted I try it too. Once inside, I shed my dress and stood before him in my sexiest bra-and-panty set. I undressed Luke slowly—he’d shaken off his surprise—and then we climbed into bed together. I took his cock into my mouth, deep-throating him until he begged me to stop. He pushed me onto my back, removing my underwear, he licked me until I was slick and ready, and then we made love, neither of us in a rush. We both came hard, me riding on top as our bodies convulsed in pleasure.
After a breather, Luke pulled me onto all fours and thrust into me again, pounding me until I reached my peak a second time. As he neared his own orgasm, I spun around, took him back into my mouth, and swallowed the warm, creamy cum as he filled me. Exhausted, we collapsed into sleep.
I awoke to Luke’s cock gliding against my lips; I guided him inside, and we made love slowly once more, savouring our final farewell to each other and my incredible holiday.
In the morning, we showered, dressed, and went to the other hotel to meet the others. They were packing up, so we all headed to the restaurant for breakfast. Our room needed to be vacated by eleven, but the front desk agreed to store our luggage until the coach arrived. Sarah suggested we check out, stash our cases in her room, then spend the day by their pool—shower before our departure—and everyone agreed.
We had lunch, sunbathed, and Mikki and I took one last opportunity to flash our tits. Later, Sarah beckoned me into her room. Curious, I asked what she had in mind. She slipped off her wrap and bikini bottoms, inviting me for one final tryst before I left.
After undressing, I joined her on the bed, gently caressing her soft skin as we kissed passionately. My hands wandered to her breasts, teasing her nipples. She guided me onto my back, slowly moving down to my pussy, where her tongue traced the length of my slit. The sensation was incredible, and I repositioned myself to reach her pussy as well, allowing us to pleasure each other simultaneously. In just two days, Sarah had learned a lot, and with her fingers and her gentle nibbling of my clit, she quickly brought me close to climax. I licked her pussy, slipping two fingers inside and teasing her clit with my teeth, eager for her to reach the same level of excitement. As we increased our pace, we both reached an intense climax. Afterward, I teased her, saying she was definitely bi now—she laughed and agreed. We showered together before rejoining the group.
Luke took the others to the room to shower, It took Luke an hour to return with the cases—Mikki later confided on the coach that shed been well fucked by all three guys. Standing on the curb with our luggage, we waited for the coach. When it arrived, the guys loaded our bags, and we shared hugs and kisses goodbye. On the drive to the airport, Mikki and I reminisced about all the fun we’d had and the new cocks we’d sampled.
I filled Mikki in on my session with Sarah, sharing that she had made significant progress in just a few days. Then, Mikki recounted what happened when they went to the room. As Mikki got ready to shower, James and Bobbie also undressed to shower and went ahead first. While waiting, Mikki noticed Luke admiring her naked body. He quickly undressed, and without any foreplay, they jumped onto the bed. Luke guided his cock into her, and they began a fast-paced, lust-driven encounter until Luke climaxed.
As Luke pulled out, Bobbie emerged from the shower. Seeing Mikki on the bed, he took Luke’s place. This was another quick, lustful encounter, and soon they were both reaching climax together. As Bobbie got off, James entered the bedroom. Looking at Mikki, he teased, "You greedy girl."
While Luke and Bobbie were showering, Mikki rode her boyfriend, expressing how much she loved him. Soon, they were both building up to a final high, and as Luke returned to the room, James thrust deeply, filling her with his own cum—her third load. This pushed her over the edge, and she had an intense orgasm.
Quickly, they both showered, dressed, packed, and joined Sarah and me. That's what she told me on the coach, and knowing Mikki, I was sure she wasn't exaggerating.
Sarah and I swapped addresses and phone numbers, promising to stay in touch. As it worked out we wouldn’t meet again until after Bobbie and I move back to Cornwall, so there’s more to look forward to in future stories. At the airport we passed through security, stocked up on duty-free, and settled down with a bottle of bubbly. After our in-flight meal, Mikki slipped off to the rear toilet followed closely by Bobbie. When she returned, she whispered all about their mile-high club adventure over a G&T.
This is what she told me: ”As they slipped into the dimly-lit restroom at the back of the plane, she was sure no one noticed. Once inside, she locked the door and sat down, quickly unbuckling Bobbie's belt and pulling down his trousers. She took him into her mouth, bringing him to full arousal. Standing up and turning her back to him, she slid down her panties and leaned her arms on the seat. Bobbie lifted her dress, taking in the view. She guided his cock into her, and soon he was thrusting eagerly. After a moment, he whispered that he was coming, filling her pussy again with his cum. She cleaned up as best she could, pulled up her panties, washed her hands, and they exited the restroom”.
The remainder of the flight passed without incident, and we landed and drove home, reaching our destination shortly after two in the morning. Exhausted and exhilarated, we finally crawled into bed and slept.
On Sunday, we got up early, unpacked, and started the washing before walking over to Sandra's to pick up Oliver. We had both missed him. Finding no answer at the door, Mikki let herself in, concerned, only to find the house empty except for a note in the kitchen from Sandra. The note assured us that Oliver was fine and that John had invited them to stay while we were away. We were to pick up Oliver upon getting the note. We drove over to John's place, fully aware of Sandra's situation and why she was staying there.
When we knocked on the door, it opened, and Oliver came running to his mom, giving her a big hug, then he hugged me and asked about presents. We all laughed, and Mikki promised him he could have them as soon as we got home. We thanked Sandra, and I wished her a good day, reminding her to take things slow, knowing the challenges ahead for her.
Back home, the guys were planning to head to the club. I teased them, asking if they hadn't seen enough naked women already. Laughing, they insisted they were just going to meet friends, so Mikki quipped, "So no watching strippers, then?"
We gave Oliver his presents, and his face lit up as he unwrapped a hat, a donkey, some sweets, and a toy plane. He happily went off to play with them. There was no need to cook a meal since the guys had planned to pick up Chinese food to wrap up the holiday.
Mikki pulled out the list and started ticking off the challenges we had completed during our exciting holiday. In order of completion, they were:
- "Number 17: Walk naked on a nudist beach" – checked off many times!
- "Number 6: Fucked by three guys at once" – checked!
- "Number 16: Fuck four guys one after another" – checked, we did six!
- "Number 13: Flirt with and fuck a bartender" – checked, we did two each!
- "Number 12: Seduce a couple and have sex with both" – checked, with Sarah and Luke!
- "Number 18: Fucked on a plane, join the mile-high club" – checked, I did on the way out, Mikki on the return flight.
We both agreed it had been a fantastic holiday.
For the remaining challenges, Mikki suggested we write down the numbers, fold them up, and draw from a hat to decide what to tackle next. If something wasn't feasible at that moment, we'd simply pick again.
So far, we had completed fourteen of our original twenty-four challenges, and the list was getting shorter. Mikki and I had tackled fourteen challenges, leaving ten more to finish. We had fun with seven new cocks and one new pussy.
I thoroughly enjoyed these six challenges, doubling my experiences with men from seven cocks to fourteen cocks and with one women to four pussies.
If you enjoyed this story, please like and favorite it. Your feedback and suggestions are always welcome.
The upcoming story involves the pizza guy's wife with an unexpected twist, where Mikki and I continue to take on more challenges from the list! Carol xx.
