Our Cabo Trip (First Cuckold Experience)

If this gets 100 upvotes I’ll post part 2! Long story but worth the build up. Enjoy!

My wife and I just got back from a trip to Cabo this last week. We haven’t vacationed in a while due to the world “situation” this last year so it felt good to finally get out and spend some time. This vacation was different in many ways though. If you have been following my latest updates, my wife and I have been getting a bit more adventurous in our sex life. I have introduced a cock sleeve and my wife has been totally into looking at men with big dicks etc. Here is a link to those if you want to catch up: [Introducing my wife to bigger things](https://www.reddit.com/r/cuckoldstories/comments/mi8u9t/the_cabo_trip_first_cuckold_experience_consensual/?utm_source=share&utm_medium=ios_app&utm_name=iossmf)

Anyways, this trip was a bit different and we decided to really go all out for this vacation in a few ways. First off, we rented a penthouse at one of the resorts that was just incredible. The view from the balcony was looking right onto the resorts pools and ocean. It was cheap considering how nice this place was and that it was operating at 50% capacity.
We also got prepped for this trip by tanning a few weeks out, both getting waxed, and I bought her some skimpy swimsuits from a company called BoutineLA. These are cheeky swimsuits that you would only wear on a foreign vacation or in Vegas. My wife is 5’9” and in amazing shape so the bikinis looked incredible on her. G String bottom and the top showed a lot of underboob. Probably got a size too small but it looked sexy regardless.

We were both excited for the trip but I was also a bit nervous. I knew we had been going down a kinky path and had a fantasy of my wife fucking another hung guy in front of me. I knew that if it was going to happen, it would probably be on a trip like this where we wouldn’t run into the person again and just have a one time fun experience. My wife has toyed with the idea going back and forth a million times. She loves the idea of having a hot guy with a big dick but also wasn’t sure she could separate her emotions and didn’t want to ruin the marriage. I had asked if she would be open to doing this with someone she would never know or see again, and she said “Maybe”.

So fast forward a little, we arrive at the Cabo airport, get taken to the resort and settle into the penthouse. It’s about 11AM so we both put on our bathing suits and head down to the pool. My wife is wearing the white BoutineLA bikini I got her. Her firm ass is completely exposed and the top is covering her C cup tits but leaving some space below for the underboob. We get down to the pool and the attendant takes us over to a couple of lounge chairs near one of the main pool bars. The pool had a decent amount of people there. Mostly Americans and Europeans couples from 25-55 years old.

There was also a group of guys in the pool with beers in hand. It looked like a bachelor party of sorts since there was about 7 guys in the group and no women with them. They were tossing around a football and chatting as they pounded beer after beer.

We sat down in our lounge chairs and my wife took off the robe she wore to go down to the pool. She looked insanely hot and was by far the best looking and most in shape woman at the pool. Instantly I saw everyone in the area start looking over as she was standing there in her g string starting to put on sunscreen. Among the people looking were all the guys from the bachelor party that were in the pool. I heard some whispers and giggles as their conversation died down and the ball wasn’t being thrown. I mentioned to my wife “You have some admirers”. She turned and looked at the guys in the pool and waved! They all instantly looked away and the ball resumed to be thrown. My wife and I had a good laugh as we sat down and the attendant came over. We ordered some drinks and enjoyed getting some sun.

After a few hours of drinking margaritas and catching some sun, a hotel employee came by and let us know his name was Marcelo. He was the director of resort activities and was organizing a chicken fight tournament in the pool (for those that don’t know, a chicken fight is when a woman gets on a mans shoulders and they wrestle an opposing couple. The first team to fall or topple over loses).
My wife was pretty tipsy at this point and instantly sat up and said “Babe! Let’s do it!!!”
I was also pretty tipsy and just told her I wanted to relax but that she should go play if she wanted to. She stood up and said “ok!” And proceeded to follow Marcelo towards the pool. Again, as she walked around, all eyes were on her and her skimpy white bikini.

I ordered another drink and sat up to watch the little tournament that was about to take place right in front of my pool chair. Several different couples had gathered around at this point. Most of them in their 40s-50s. It seemed that my wife was the only solo participant (scumbag move on my end I know). Marcelo the resort director talked to her for a second and then turned to the bachelor party in the pool. “Do any of you gentleman want to be this beautiful woman’s partner in a chicken fight?”
Most of the guys in the party laughed a bit and looked at each other. Eventually what looked to be the leader of the group waved his hands to silence everyone and said “Alright guys I’ll do it! But if we win you all pay for my drinks for the rest of the stay!” They all laughed and nodded as the leader waded over to the pool steps and climbed out. He walked over to the participants of the tournament and eventually to my wife and shook her hand. They talked for a couple seconds introducing themselves. What I didn’t know, is that this introduction would change the rest of our trip, and lives.

My wife’s parter for the tournament stood next to her as they all listened to the rules. He was about 6 ft tall with an average build. Not too muscular but you could tell he worked out. He had a black pair of swim trunks on and a black backwards trucker hat. Under the hat he had brown hair that was slightly long. Eventually Marcelo finished giving everyone the rules and he announced the first two teams that would face off in the first round. My wife came over just then to take another sip of her drink. She was giddy and excited to play as she told me the prize for winning would be a dinner at their best restaurant the resort had. I then asked “Who’s your new friend”? A smile came over her face as she responded, “His name is Conor and he’s actually from the UK here for his own bachelor party!”
“Oh so he’s engaged” I said with a bit of relief in my voice.
“Yeah! Seems like it! Ok babe I’m up next so I wish me luck” my wife said as she turned to go back and join Conor on the ledge of the pool as they scouted their opponents. Truthfully, as much as I liked the idea and fantasy of having my wife sleep with another man, the reality of it scared me to my core. So many things ran though my head but I instantly reminded myself that Conor was engaged.

After the first match ended it was now my wife and Conors turn to enter the pool against their opponents. They were both pretty drunk and giddy at this point. Laughing as they got in the pool and prepared to wrestle their other team. Conor then went under water and my wife climbed up on his shoulders. Her legs were straddling his head as he stood up with her on top of his shoulder. Just then I realized, the bikini I bought for my wife was soaked and very very veryyyyyy see through ?‍♂️. Her nipples were clearly visible through the top of her bikini as Conor moved around the pool to get in position. My wife had no clue as she was pretty drunk and also preparing to wrestle the opposing couple. Conor turned around and of course my wife’s Bikini bottoms were see through as well and exposing her ass.
My wife and Conor braced themselves as the match began. The opposing couple were about 40 years old and not in very good shape. The match started and Conor makes his way over to the other couple with my wife on his shoulder. Instantly the two women lock hands as they try to throw the other one off their teammate. My wife gave the other woman a big push as Conor kept driving forward. SPLASH!!! The other couple toppled over very easily. The spectators cheered as my wife and Conor screamed in victory. My wife got off Conors shoulders and turned toward him with her arms in the air as they both then gave each other a congratulatory hug. They continued cheering and Conor turned to his buddies “You’re all going to have to pay! Just watch!”

The matches went on. My wife and Conor made easy work of the other couples they faced up against. Each time the won, they would hug each other tighter and tighter. Eventually Conor was picking my wife up and she would straddle him as they paraded around after each victory. My stomach at that point was in knots. I had lost my buzz and now all I could think about was my wife being overly touchy and flirty with some random guy. At this point there were about 100 people gathered to watch the chicken fight tournament. Not sure how many were there for entertainment or how many were there to see my wife in a see through bathing suit, but nonetheless I didn’t want to make a scene since we had a week left there.

We were now at the final match. My wife and Conor vs another 30 something couple that had also been sweeping their competitors. The match started and the two women locked hands and wrestled as the men fought for position and to keep the women on their shoulders. Just then, it looked like Conor tripped and started to fall back. The opposing woman gave my wife one big push and that was all it took. My wife fell off Conor and he sunk underwater as the other couple cheered in celebration. They had won the tournament and the dinner at the restaurant. At that point I was relieved it was over and ready to get back to the room with my wife.

As my wife and Conor came up from being underwater, I noticed that my wife’s top had fallen off from the push and splash! She had no idea since she was just underwater and still really drunk. Conor stood there and said “Oh shit! Your top came off!” Instantly my wife covered her breast with her hands as Conor searched for the top. He quickly found it and started to help her get it back on. He then helped her tie off the back. My heart was pounding as I got up with a towel and rushed over to her. I know when she got out of the pool her see through bikini would expose everything to the crowd. She walked up the steps and I quickly covered her with the towel and started to walk away with her. She was visibly drunk and laughing as she got out. “Babe did you see how far we made it? It was so much fun!!!” She exclaimed.
Yeah babe it looked like a blast. Let’s get you upstairs for so we can nap before dinner. I quickly turned around and saw Conor standing with his buddies. He and I both exchanged looks as I turned again to bring my wife up to the room for a nap and some water.

Fast forward to that evening we woke up late around 8:30pm. We quickly got dressed and decided to go down for dinner. Despite my wife losing the tournament earlier, I was still craving a meal from the restaurant that was offered as the winning prize. We headed down to the lobby to get a reservation. Upon being seated I glanced over and saw the winning couple from the day seated a few tables away from us. We waved over to them and they waved back. “Did you have a blast out there today or what” I asked.
“Yeah it was a lot of fun! Maybe too much fun haha” she replied.
Me: “what do you mean too much fun?”
Wife: “Well obviously I was drunk and my bikini was see through. Never thought I’d let so many people see me like that.”
Me: “yeah it was a show for sure. Seems like you and that guy got pretty friendly too!”
Wife: “yeah he was a cool guy. A bit excited at times.”
Me: “what do you mean?”
Wife: “well, there were a couple times when we won and celebrated…. I think he had a boner…”
Me: “Oh yeah? Was he big?”
Wife: “Umm… yeah it was decent sized” she said with a smirk…

We finished the meal and started on some glasses of wine as the conversation moved to other things. Before we knew it, we were tipsy again. I asked the waiter for a bottle of wine to go and we paid our tab and walked down to the beach. We sat on a couple of chairs as the waves crashed in front of us. I poured each of us some more wine. Just then something came over me as I felt more secure now that Conor was nowhere in sight. Maybe I was a bit horny too.
Me: “So what did you think of that guy today? Your partner.”
Wife: “Oh he was nice. Sad we didn’t win.”
Me: “no I mean what did you think of him? We’re you attracted to him?”
Wife: “oh we are going down this road again huh? Haha!”
Me: “I just wanna know! Seems like you guys were pretty touchy in the pool.”
Wife: “Yeah I guess the booze and atmosphere got the best of us.”
Me: “cmon babe! Give me something here! It’s ok if you thought he was hot. It turns me on to know. Cmon already. Spill the beans!”
Wife: “Haha ok ok I guess he was pretty cute.”
Me: “yeah? And his dick was just decent?”
Wife: “Well I may have undersold that part. He was as big as one of your sleeves you use on me.”
Me: “Really!?! Like 9 inches and thick?!”
Wife: “yeah I mean I was only hugging him but there was a point where he picked me up and we were facing each other. I felt his dick right up against my pussy and stomach. Seemed really big.”
Me: “wow… did it turn you on?”
Wife: “Yeah in the moment I was shocked and didn’t know what to do. Lots of people around you know? But yeah now definitely it makes me horny thinking about it. His fiancé is a lucky lady.”
Me: “Hear me out on this… what if I said it was ok for you two to fool around a bit? And maybe he was down with it as a last hoorah before he gets married?”
Wife: “Haha you’re nuts! He’s getting married there’s no way he would do something like that!?”
Me: “well what if he was. Would you be up for it?”
Wife: “Haha yeah sure. No chance he’s up for it since he’s probably a faithful guy. But sure… if he is up for it and you’ll be in the room I’ll give him head. And That’s IT! I’m serious babe nothing beyond head!”
Me: “Ok fair enough. Cheers ? “
Wife: “You’re crazy! Cheers ? “

Source: reddit.com/r/Erotica/comments/mijp78/our_cabo_trip_first_cuckold_experience