Fishing trip.

So, a bunch of my buddies and I were talking about going on a fishing trip. The problem we were facing was that we wanted to take one of the larger charter boats. They usually offer better amenities and also a better time. The issue was the cost. We were looking at going from 130$ per person to almost 400 per person and that was going to be hard for most of us. But we figured we could get hooked up with maybe a few more people at the marina. If not then take the cheaper one this time out and try to save for the more expensive one later.

Trip day came and we met at the airport. As always, it’s a pain in the ass getting though security and then on board. But 2 hours later we landed at Cancun intl. The lines always suck ass going through immigration but it usually goes pretty fast. Once though that we grabbed our hired car to the hotel. We stayed in the Westin. 4 rooms all over looking the beach and the pool. It was a great first day. Had a nice bar b q that night and then sitting by the pool having drinks and watching the ladies getting in and out of the water. A number of them caught our eye and we enjoyed quietly rating them on a scale of 1 to 10.
We had a few hours left before hitting the sack when we noticed a man and woman walking down the pool. Behind them were 3 of the hotel employees carrying a cooler, towels and some sort of pillows. They set up directly across the pool from us and at the point we were its not very far so we could see clearly. The man was in his mid-fifties. The lady in her maybe late 20s. She also had an awesome body on her. Tall with long legs. Big tits that could barely stay in her bikini top. Long and very thick black hair.

We watched the couple for about 20 more minutes and all of us staring that the woman as she walked into the pool, got her body wet while holding her hair up a little. Then came back out. I think I heard a sigh from the other guys as her boobs broke the top of the water. We could see it sluicing off her mounds. It was so hot to watch. It was not until that point that we saw her from the back. Her ass was big and round and packed into the bikini bottom. But the bottom was a thong so it was just the perfect shot. I think all of us were hard.

The next day we woke at about 6 in the morning and headed down to breakfast at the palapa by the pool. Sitting waiting to be served the woman from the night before walked up and was seated alone just a few tables away. She waved to us as she sat down and we were all a bit surprised but we greeted her anyway just to be polite. A few minutes later we were served and our conversation turned to the day and what we would be doing. It was Fishing trip time and we wanted to have fun. We started talking about the price of the bigger boats and what amount we could all put in. By the end of the conversation we figured we were going to be about 430 dollars short for the big boat. The problem was that the regular size boats were nice but a bit cramped for us. The big boats were amazing and honestly to big but the idea and all the extras is worth it. With our last few sips of coffee, we asked for the bill. To my surprise I saw the woman across the way, stand up and kind of wave to me. I smiled and watched her approach the table. She introduced herself as Samantha or Sam for short.

She was standing just far enough away from the table that we could all admire her amazing body. Tight with shorts that made her thighs look amazing. “ I over heard a bit of your conversation about the fishing trip and wanted to make an offer. How about we all go together. My Boyfriend and I were planning a trip today with a few of my friends. So lets rent a big boat.” Some how the guys decided I was the official spokes person by all looking at me for a reply. “ Well, we do not want to intrude on your romantic trip. We just want to do some fishing. I’m not sure if you heard the part where we were saying that the smaller boats were just a touch to small but the bigger ones, well honestly they are a little out of our budget.” She smiled and replied. “ No Problem.” She handed us a card and it had a marina name and address and said, “ See you at 10 at the marina”. Now I have to admit that watching her walk away was the highlight of our morning. What an ass that woman had!

I looked at my watch and announced we had time for one more coffee then it was time to get ready. All the guys agreed of course with a bit of a raised eyebrow on how things were turning out so far.
Shortly after we were all at the front of the hotel lobby getting into a white SUV taxi and heading to the Marina. When we arrived we were a bit surprised as it was a hidden Marina on the Lagoon side. Right across the street from the Shopping Mall called KuKulCan Plaza. We also happened to note there is a Ruths Chirs steak house there and that meant a place for dinner after a day fishing.

Walking down the board walkway we could only see a few small boats. I was just starting to wonder if we have been duped when we saw Sam walking up towards us. This woman was something else let me tell you. The shorts were gone and replaced with a bikini bottom even smaller than the one she had at the pool. This of course was to our Delight. However, she was wearing a shirt that was to the top of the bikini bottom but also with long sleeves. The kind from full sand. She said hello and to follow her. The peir is not that long and the boats at the end were getting bigger and bigger. Honestly, we all started to get nervous. When we got near the end the boat in the last row as not a boat it was a ship. Thank god that Sam stopped at a boat three rows before. Standing on the back deck of one of the biggest charter fishing boats I have ever seen was Sam’s friend or husband, we did not know yet which. She stepped aboard and motioned for us all to board. With a little help from the staff we all got on. This boat was about 87 feet long. Actually more of a Yatch but it had been geared up for fishing.

Once we got onboard Sam Introduced is to her boyfriend David Paak. He said he was visiting from Canada and was happy to have us go along. Then he looked at Sam and asked when her friends would arrive.
Standing there I realized this was a lot of boat for my group of 5 and her and her boyfriend. So, I asked her if we could talk. She motioned me into the Salon below while the other guys got situated on the deck and were served cold drinks of Juices and fruit while we waited.

Sam and I on the other hand were down I the main salon and I realized right away that the air conditioners were on and it was quite cool. I looked at her and raising my hands in a placating way. I said. “ Sam, I don’t think my guys and I can afford half of this. I think its way out of our league.” She smiled and told me to sit down. And then asked if it was ok that she changed. I was a bit caught off guard but said ok. Sam turned around and picked up the bikini top that matched the bottom and I could see already it was as small and sexy as the its bottom counterpart. I expected her to either put it under her shirt or to turn around. Instead she just took the shirt off. I sat in awe looking at some of the prettiest, biggest and most perfect tits I had ever seen in my life. She smiled at me and proceeded to put on her top that looked more like a rubber band than anything. I could barely cover her nipples which were small anyway. She looked me right in the eyes and asked if I liked what I saw. I kind of stumbled over my words but finally got out a Yes!!! “ Good”. “ Now give me the money you were planning to spend and we will use it to tip the staff. Otherwise everything is taken care of. Just make sure to thank David before you leave.” With that, she turned to show off her amazing ass and walked back out to the back deck. I could see some of my friends trying not to stare.

Once back out in the sun I grabbed a cool drink and approached Daivd. I extended my hand and opened my mouth to say thank you and he replied before I could. “ Don’t mention it. I love making people happy and especially Sam. She wanted you here so you are my guests. Everything is included so enjoy!”

I walked to the back of the boat and stood looking down the line of other vessels. I guess I was deep in thought because it took the sound of Sam’s cell phone ringing to make me realize I was looking at five of the most beautiful and built sexy women I had ever seen walking towards me and the boat. Sam let out a squeal and ran to stand beside me. She reached over and pinched my arm and said these girls are for you guys. Your going to love them and you do not have to worry. What happens in Cancun stays in Cancun and then she tapped my ring finger. I smiled shyly as a man is wont to do.
The ladies that came aboard to say the least where hot. Most of them wearing some sort of jean shorts and heels although they were not high heels. Just low cut but sexy as well. All of them seemed to have had the biggest boobs ever but that may just have been my smaller head thinking for me. No matter what they boarded and were introduced around. The girls and my friends seeming to be happy. I noticed looking at the girls that they were tall and beautiful elegant but playful and having a great time before the boat even left the marina. I also noticed that Sam never left my side. This I found a bit odd as she was with her boyfriend on board.

The boat set sail and all the girls were in various types of bikinis. Some of them like the ones Sam was wearing, while others had on something more modest. Once we left the dock the drinks were poured again but this time with a generous helping of Vodka into each. This of course was served by Sam. With a smile a wink and a lot of a cleavage shot as she poured for everyone. I looked around for David but did not see him. I asked a crewmen and he said something but I did not understand so I asked Sam. She smile and this time it was her turn to look shy. She said he had left the boat and would not be going with us. He just wanted to see her off on her adventure. The guys were listening and we shared a few looks of confusion. But that was broken up with the captain announced we had about an hour and a half to enjoy ourselves before getting to the fishing area.

After sitting around and having a couple of drinks that always seemed to be full the girls invited us to the salon into the ac for some drinking games. When is sat at the table I felt the boat slow down and that was when I saw Sam come back down the stairs. I figured she just wanted some more time to talk, play what ever games they had in mind and to enjoy her day out. Everyone was seated and Sam sat next to me. She put her hand on my shoulder and announced the first game would be drinking to Liar Liar. I noticed while she was talking that everyone was sitting boy girl.
Apparently, the game goes like this. The first persona says something about themselves. If it’s a lie and we catch them they drink or it’s the truth and we call it, we drink. So, of course Sam started the game. Her first statement was, “ This is going to be an awesome day!” Everyone tipped back their drinks and enjoyed a nice laugh. The next was a girl name Nancy. She stated matter of factly that her boobs were a triple D. Once again everyone shared a drink.

After a little while the game slowed down as we were easily able to guess truth from lie. It finally made its way to Sam again and she said she wanted to change the game a little. She wanted to know personal things. Then she started out. And I think this is where things turned very interesting. Sam stood up and looked us all in the eye. Raised her glass and announced very clearly that she was Trans! Of course all of us called it a lie. She raised her cup to her lips and was about to take a drink to show that we had caught her telling a lie but then stopped and pulled off her bikini bottom instead. She had a cock and it was big. Honestly, I had been flirting with her all day and she had rubbed her boobs against me so many times that I got hard over and over. Now I was a little shocked and did not know what to do.

Right before Sam’s Bomb of a comment I had noted all the guys and girls were in some way connected. Holding hands or an arm around the other. I had even seen Brad kissing Karla. That was when it hit me like a ton of bricks. All the girls are trans. So, because it was my turn that’s what I said. To my surprise every one in the group took a drink. Apparently, I was the last and only one to not know. My friends knew and accepted it very easily. After all these women were stunning to look at.

With that the game kind of ended but the guys seemed happy to sit and chat with the girls and each other. Sam announced that she had asked the Captain to not only take the long way but allow us into the late evening. Then she stated that the boat had 5 bedrooms. I got up and walked back out into the sun. I was not really upset but I did not know how to react to these people. Lets face it most men on the planet have thought of what it would be like to be with a perfect trans girl and everyone of these were. It was peaceful watching the water go by. Standing alone with my thoughts as the sun beat down on my back and shoulders. Then a hand gently touched my arm and a cup with a new drink was placed into my other hand. I looked over to see the very beautiful Sam standing there. She smiled and put her head down a little. Then said she was sorry.

Sam turned and walked back into the salon and I watched her out of the corner of my eye. Honestly, I had never seen a more beautiful woman. I was not mad. I was not… I don’t know. I just did not know what I would do with a trans woman. But talking and not being alone was a nice idea so I headed back in. When I got inside I noted that we were alone. Apparently Brad and some of the other guys were up front in the sun with the girls and apparently Keira and Tomas where in one of the rooms.

Sam and I sat across from each other and she asked me how I was feeling. She said that all the guys seem to be ok with this and that she had not wanted to shock me or scare me. That when she saw me at the hotel, that she could not take her eyes off of me from across the pool. It made me smile and I confessed that it had been the same for me. But now I just did not know how to proceed. I did not want to treat her like one of the guys but it was a little odd to keep thinking of her as a woman. Sam looked at me and said. “ I am a woman just with a little extra for fun. “ She giggled, and then refilled our drinks. Of course as she moved I could not keep my eyes off of her amazing body. Once she sat back down this time right next to me placing one hand on my leg and the other with her glass.
I was astounded that in what felt like just a few minutes the Captain announced that we were arriving at the fishing area and for all hands on deck. I guess that meant us as well because everyone reappeared. Some like Brad with a sheepish grin. The others toasty from the sun and grabbing new food and drinks.

The fishing went well with the ladies bagging 7 sail fish to the 5 of the men. We also landed 1 small shark and a number of other fish. The crew was amazing and off with the fish in a flash to prepare dinner and anything that we wanted shipped home. As the suns set we dined on wine, fish and veggies and a lot of laughter and fun. I could clearly see the guys were more the comfortable with the ladies. Kissing and holding hands. Touching each other in public.

All of the ladies announced they would be heading off to shower as the boat turned towards home. Some of the guys with their respective new lady friends. Some sat waiting and chatting. I had moved to the back of the boat again and was told I would be notified when a shower was available again.

After a few minutes I was told by a crew member that Suite 1 was available for a shower and changing. So off I went with drink in hand. The other people were scattered around the boat doing all sorts of things from playing cards to kissing and making out on the sofa. I excused myself as I went through and into the suite. The room was amazing and actually quite large. I could hear the fans running to ventilate the bathroom and I dropped my bag on the bed. Then taking off my topsiders I slipped my shorts down and dropped my shirt on it beside my bag. I then grabbed my travel clean up kit and opened the bathroom door.
It became almost instantly apparent to me that I had not heard what I thought I heard. The shower was running and not a fan and inside that shower was the unmistakable form of Sam. She slowly opened the door and took my hand and pulled me in. Without a bit of hesitation, she stood on her toes and kissed me. I noted that her cock was tucked back but her boobs were out, wet and her nipples were hard. She kept kissing me and touching me and to my surprise my cock started to harden in her hand. That was when I decided to just let things go and see what happened. I started really kissing her back and enjoying her soft lips. Her tongue as it went in and out of my mouth touching my. The water continued to pour over us and she started to soap my body. Kissing my shoulder as she worked her way down to her knees.
Sam used the soap in her hands to wash my body and then work her way back to my cock. By that time it was rock hard and honestly harder than I had been in years. I felt like I was 19 again. I did not think I could get harder until I saw her lips cross the top of the head of my cock and she swallowed it. I could feel it hitting the back of her throat making the curve down and deep. So hot and wet. I turned off the water and leaned back against the wall and just watched as she moved her head in the most amazing ways. My cock was on fire with passion and desire to blow my load. Her hands never stopped caressing my body. They went from my balls down to my feet. Up to my chest and then to my ass. She even used her fingers to caress my ass hole which was another first time for me. I was interested to see that it turned me on to have her fingers doing that.

Sam started to stand back up but was sucking so hard on my cock that it actually made a popping sound as it escaped her mouth and perfect lips. She kissed me again and moved closer to me. Because she is actually shorter than I am, I could feel her cock pressing against my balls and then sliding by them and the inside of my thigh. She was gently moving her hips and thrusting her cock in and out. I finally reached down and for the first time in my life touched a trans cock. Sam was hard. Smoothly shaved and gasped as I touched her. I had my other hand on her breast gently pinching her nipples. We were completely clean but still kissing and stroking each other when Sam opened the door. She did not bother toweling off she just held my cock and pulled me to the bed. Then she gently shut the door and turned off the lights. I honestly did not know what to expect.

Sam slid up on the bed next to me and started kissing me again. Once again and without hesitation now I kissed her back and very deeply. My cock had not softened a bit in that few seconds and I was happy for that. I was laying on my back and she was next to me. I heard her slide the drawer open on the stand next to the bed, and then the unmistakable sound of a lubricant bottle opening. With that my heart started pounding as I had no idea what she was expecting. I know for sure having a cock in my ass was very frightening. To my relief she reached behind herself and put the lube on her. Then with one swift movement she was on top of me with my shaft sliding deep into her love hole! She started moving up and down slow at first but with an ever increasing tempo. I could feel my cock sliding in and out of the tightest hole It had ever been in. The more she moved the more I loved the feeling. For a few minutes she would move up and down really fast. Thrusting her nipples right up to my mouth and then down to her lips as my cock dove deep again in her ass. The pressure was building and I did not want to disappoint her so I told her to slow down or I would cum. She smiled and said she was about to anyway.
With that statement I stopped her by holding her down and shoving my cock deep into her. I could fell her whole body shudder. I held her like that until her breathing started to slow. Then I took my right hand and wrapped it around her cock and gently started to stroke her. She leaned back so that her entire shaft was thrust up and forward and allowed me to stroke her cleaning and without touching our bodies. As her breathing became stronger again, I would slow down, and then when her breathing slowed, I would stroke her faster. After about 10 minutes of doing this to her she finally shot a load of cum that actually hit the pillow on the other side of the bed. And that was not the end of the milk. It kept flowing down over my hand and onto my body.

Sam then climbed slowly off of me and took my cock into her mouth again. Just like the first time, her head moved in ways I had never felt. I was getting closer and closer to blowing my load. I did not know what she would do so I told her I was going to cum. This made her move faster and in more exotic ways and I finally exploded. The force was enough to make her choke and start spitting the cum all over me. It was the hottest thing I had ever felt or seen.

We laid on the bed for a little while kissing and touching each other. Then we finally showered. When we left the room we realized we were the only ones left on board. Everyone else was gone but the captain. He handed us a note from my friends that simply stated “ Bring her to the Hotel”.

The next words out of my mouth were “ Taxi!!! “ as I pulled Sam as fast as I could to the street.

It was going to be a long fun night and it was. But that is another story!