Cancun Vacation

Cancun Vacation.

I went on a family vacation not long ago and we had a nice time for the most part. Being recently broken up with my girlfriend my family thought it would be a good idea for a Cancun Vacation. So being invited I decided what the hell. This could be nice to get away. Get some sun and get some rest and clear my mind. It was to be the best Cancun Vacation ever!

We arrived on our Cancun vacation on a Sunday and the airport was slow. Do not get me wrong there were probably at least 500 people. But it was quiet and subdued and fast. We got our bags and got out. As I was walking out to the van. I saw a girl with a few friends. Already with drinks in their hands and laughing and enjoying the day. The reason I only mention then one is because she was very sexy. HOT with big tits and long hair. The exact kind of girl I like. But no matter how hard I tried I could not catch her eye. She got into one van and I got into another that that was that. But man was she hot.
Finally, we arrived at the hotel and went though the normal check in and I guess I was lucky as I was the only person in my room. My parents had said I might need to share with my cousin. But I got lucky. And did not know how lucky I was going to get! The room opened right onto the beach and I could just walk about the door. The rest of my family was 1 floor up but about midway down the building, while I was on the corner. Just enough separation. This was for sure going to make my Cancun vacation better.

Sliding into the pool gave me instant relief from the heat and also afforded me a view of all the ladies around the pool. While I would love to tell you, I saw the girl from the airport then, I have to admit that I did not. I was keeping an eye out for her though. In the mean time I was keeping an eye on all the girls. There was ass and tits everywhere and I was loving it. A few girls nodded at me and a few said high but I was not thrilled with any of them.
A few hours later the family had informed me it was time to get ready for dinner so I headed back to my room. I was a bit tired and I was hungry and I had just enough alcohol in me to want to relax in a hot shower and get clean. So I did. One of the amazing things about a hotel is the long hot showers you can take.

I think I was in 30 min or so but I was feeling good. I thought I heard someone knock but figured I would ignore it as it was most likely just my cousin just wanting to borrow something. I toweled off and walked into the living room of the suite and turned on the tv. And again, I head the knock. It was a bit soft but there. I walked to the door and peeked out the hole. I could not really see well but it looked like the maid. When I opened the door, I was confronted with a girl wearing a bikini and holding the bottoms on with both hands. She seemed to be crying a little.
I opened the door a little wider and looked at her. Asking if she was ok and if I could call someone for her. She whispered no and that she was just hiding from some teen boys that had yanked on her bikini and broken the strap. Right as she was telling me this, we heard them yelling and running in the hall way. She more of less shoved me inside and closed the door. Then sheepishly looked up and me and said, Sorry. I don’t want them to catch me and take my bikini bottom. I can’t have that happen.

I had stepped back from her and was looking at her with a small and unsure smile on my face. She must have noticed because she looked up and said “ What”? I told her that I understood what it would be like to lose the bikini bottom but it would not be the end of the planet. She said. Yeah or at least then end of her vacation and she started to cry. I gestured for her to use my bathroom and fix it. Then I went to sit on the bed to wait.
A few minutes later she walked out with her bikini bottom secure. I got up and headed for the door to open and let her out. She put her hand on my chest and said thank you. Kissed me on the lips and walked out the door. Thank god, I don’t expect anything from any one and especially now for people to be normal. But she was gone I was hungry and heading to eat.
Two days later I was at the pool. Enjoying the sun and drinks and all of a sudden, I felt someone pouring something liquid on my heard. I moved away as fast as I could and turned around to find the girl standing over me and smiling and laughing. She squatted down and waved me closer and handed me another drink from the bar. She then stuck out her hand and said. Hi I am Dana and you rescued me a couple days ago. Those boys left so I am back out for some fun and I wanted to say hi and thanks. I really appreciate it. She then slipped off her little dress to reveal an amazing body. Small but firm natural tits and a tiny little bikini bottom that was so small. And the best part was it was a thong. So I could see it all.

We spent that whole day playing games in the pool other the other guests and getting drinks from the bar. We talked some when we were not playing but we had a great time. Several of the games involved being close and I really started to enjoy those. Feeling her body against mine from time to time. The way her ass would shove back against me and then push off. It was hot and I was loving it and it seems Dana was as well.
It started to get late and the sun was heading down. And right about that time I was waved at by the family and told dinner was at 7:30. Dress was casual formal and to bring the girl. That kind of shocked me as I had not seen my family all day and Dana was at the bar getting more drinks. When she slipped up beside me, I told her that my family had invited her to dinner with us.
I guess that was a bit of a shock to her as she kind of pulled away. Then after just a few minutes she climbed out of the pool and started to towel off. I was still in the water and she came to the edge and sat down. She took my hand and pulled me over but then dropped my hand. Looking into my eyes she told me. “ I would love to go to dinner with you and your family. My room is 1134. I will be ready and waiting at 7:15. But I need to tell you. I am trans. I still have a penis. If you don’t show up, I will understand.” With that she stood and walked away.

I could not believe what she had said. In fact I was pretty sure she was joking and screwing with me. But while I showered and rested I could not stop thinking about the day we had spent in the pool. I had held her body against mine. I knew it felt great and I also believed that if she really had a cock I would have known. So I called her room number and told her. “ See you in 20 minutes.”

When I got to Dana’s room she opened the door wearing a beautiful sun dress. It was tight at the top and flared at the bottom. She had on high heels and just a touch of makeup. We walked to the steak restaurant and as we did she took my hand. I looked at her and asked. “ Were you kidding about what you said earlier? “ She said know and moved to drop my hand. But I kept it tight and continued to walk with her. Her hand was warm and soft and comforting.

Dinner was amazing and my family treated Dana as though she were a member. We all laughed and had a great time and we drank a lot of wine. But we also ate t ton of food so the 5^th glass was just starting to make me feel it. I went to refill Dana’s and she said no she could not drink more. And kind of giggled. I looked at her with a strange look and she whispered. I will show you. Don’t freak out. Then she kind of ignored me again. I started talking with my dad and I felt her take my hand and I gave it freely. But then she did an odd thing and she opened my hand palm down and pressed it down onto her lap. I realized then what she was doing because I could feel the head of her cock sticking up. I did not jerk my hand away in fact I pressed a little harder when I turned to her. She whispered that she gets hot and horny when she drinks and she needed to stop to get the erection to go down. I gently rubbed my hand across her lap a few times until a moan escaped her lips.

We left dinner about 45 minutes later and my family went to one of the shows. I asked Dana if she wanted to go and she said no. A nice walk would be better so off we went around the gardens. We walked and talked for a while and finally found ourselves sitting on the one of the benches in front of the ocean. Watching the waves roll in and the moon rise.

I don’t really remember how it happened but at some point, Dana leaned in and kissed me. I was a bit surprised and not sure if I wanted to go that far with a trans girl but. I decided after touching her cock I might as well. So, we started kissing. The next thing I know she is in front of me on her knees and opening my pants. I had not realized that I was rock hard. She popped my cock out and it went into her mouth so fast. It was just amazing. Her hot wet lips sliding down over the head of my cock. Feeling her teeth brush over the shaft as she took it all the way down her throat. And then she started moving her head faster and up and down as my throbbing cock slid in and out of her lips.

I was in such an orgasm ready daze that I don’t even know how long she sucked my cock. But I warned her I was going to cum and she only moved faster. I shot my load down her throat and filled her mouth I was so hot and horny. She smiled and then leaned back and I notice a small shiver cross her body. I asked if she was ok and she smiled and said yes. “ I just had an orgasm as well in my panties.”
I could not believe her so she lifted her dress and I could see the cream filtering though her cute little pink panties. It was so hot.

There is a lot more to this story and I am sure you can guess the rest. But as soon as I can I will post more about the last 3 days we spent together. In the meantime. Maybe its time for your Cancun Vacation!