My Asian girlfriend Winnie and I were twenty-four years old when we went on our first vacation. It was a group trip with our friends, five other couples and two single guys. We went to Cancun and stayed at the Riu.
We immediately noticed topless sunbathers, some who looked very hot and others who were out of shape with saggy breasts. I noticed Winnie paying a lot of attention to them and told her that her boobs looked way better than these women.
We started the day hanging out on the beach drinking and lounging. The guys all went in the water while the girls laid out and tanned.
We had a good time checking out all the women, especially the ones who were topless, until my buddy Andrew said quietly to me, "You better go check on your girl."
From far away, I could see that my girlfriend had taken off her top and was laying out topless. I was shocked and quickly walked back to her with the guys all following me. As soon as she saw us coming, she flipped over to hide her breasts. I sat down next to her and the guys sat next to their girls, but everyone was awkwardly quiet. Even though she laid with her front down, she looked so sexy with her bare back exposed and her scrunch bikini bottom tight between her ass. Her nipples were hidden, but you could still see the side of her breasts pressed up against the ground.
Andrew, who was single, sat down next to me and right above where Winnie was laying. I asked him if he saw anything, and he looked at me with a smile and nodded.
Winnie looked up at us asking, "What are you guys talking about?"
She positioned herself up on her elbows giving us a perfect view of her tits dangling. I had a feeling she was doing it on purpose to tease Andrew. Shortly after, she put her top back on, disappointing the guys who were also waiting for a peek of her.
The next night, we all got together for dinner and had rounds of Saki Bombs. Some of our friends got sick and had to go back to their rooms. The rest of the group headed to the resort disco and took some more shots at the bar. When we left the disco, Winnie and one of the girls started running away. They ran around the gate to the resort pool and started undressing. I couldn't believe it, but Winnie and her friend jumped in the pool naked.
Andrew and I caught up to them, took off our clothes, and jumped in after them. The rest of the group did the same but left their underwear and bras on. It was our first skinny dipping experience, and all initiated by Winnie.
We were swimming around in the pool when I noticed the guys all trying to check out my girlfriend. I was checking out their girls too, but no one else compared. They were either short, chubby, or flat chested compared to Winnie's busty slender body.
It wasn't long until the security guard showed up. He told us the pool was already closed, and we needed to get out. Everyone quickly got out except for me, Winnie, and Andrew since we were completely nude. Winnie tried reaching for her clothes at the edge of the pool. She couldn't get to it, so she leaned over the ledge with her butt sticking up. There was just enough light for us to see her tight ass and shaven pussy underneath.
I gave her a couple of light slaps on her butt to try to get her down. Andrew, using the opportunity, slapped even harder.
She yelled out, "Ow, ow, ow!"
Winnie looked back at him, got in the water, and playfully tried to hit him back. The security guard was still waiting for us, so I got out of the water first to get her clothes for her. While putting my clothes on, I watched Winnie and Andrew play fighting in the pool. She was trying to get him back, but he held onto both her hands. It was a short ten second sequence, but it was hot seeing them so close together naked.
I handed Winnie her bra and panties and then she got out of the pool with Andrew following her. I hadn't noticed before, but his cock looked huge standing semi-hard. I could see Winnie staring at it while putting her clothes on. We all left and got in the elevator, and I could feel the sexual tension in that elevator ride. But then Andrew got out and we all went back to our rooms.
The next day, we caught up to the rest of the group for lunch. I saw Andrew at the table whispering to the guys. We sat down with them, and it immediately got quiet. Finally, one of the guys spoke up.
His girlfriend was the other girl to go nude at the pool, so he tried to make a joke about it, "I need everyone to erase from your memory what you saw last night."
Everyone laughed, but one of the guys remarked slyly to me, "Don't you need to make that same speech about Winnie."
Later that day, we went on a speed boat tour with our friends. It was a fun activity with each couple driving their own little boats. We followed the tour operator in a line, speeding around the bay.
Andrew was in the boat in front of us with Paul, who was the other single guy in the group and rooming with Andrew at the hotel.
Sitting next to me, Winnie unclipped her life jacket and untied her bikini top, exposing herself again. She was getting very comfortable being in that state of dress. It was Paul who looked back and saw Winnie first. I saw him nudge Andrew and point back to us. Even though Andrew was driving, he looked back to catch a glimpse of her naked tits. They both smiled at us while we waved back at them.
We made the final turn around the tour operator, and he also saw Winnie topless, giving us the thumbs up. While slowing down to redock our boats, Winnie tied her top back on before the rest of the group saw her.
That night, we all hung out on the beach before going home the next morning. Everyone decided to go for a late-night swim, so Winnie and I joined them. While in the water, we had a chance to talk to Andrew and Paul.
Paul, who missed out on the night before, suggested, "Let's have a redo of last night!"
Andrew mentioned, "How about a repeat of earlier on the boat?"
Winnie had a big smile on her face, clearly embarrassed, but she didn't say anything.
Two other guys joined in our conversation. They all wanted to go skinny dipping again, hoping to get another peek of Winnie naked.
I asked them, "How about the other girls?"
The two guys with girlfriends said, "Let's leave them out of it."
