My First Time Cuckolding as a Sugar Traveler

I am a 23-year-old Sugar Baby, and I recently decided to try a Sugar Travel site. The site I was on had so many great offers to join various Sugar Daddies on a free all expenses paid trip. I had not had the luxury of much travel in my lifetime, so this concept really appealed to me and I decided to jump in immediately.

After many offers it was a man based out of Minnesota who caught my interest. He wanted to travel to the Dominican Republic and was recently divorced. I live just outside of Chicago, so the downside of us meeting was the fact that we would not meet until it was time to travel.

As such, we spent a great deal of time chatting with each other and also talked on webcam on several occasions. He was a great conversationalist and we had many things in common even though that we had a 27-year age difference. I admit, the age difference did bother me at first, but he was just so nice that shortly after talking I really didn’t even think of it.

One thing that stood out about this Sugar Daddy was that he never once talked about sex. Compared to most men who had been communicating with me on this site I found this a little unusual. I mean, I knew that many men would be wanting not just companionship on their travels, but that many men were interested also in a potential sexual relationship. I hadn’t offered anything of the kind, but like most Sugar Babies I was open to this.

So finally, it was time to travel and I was so excited to be going to the beautiful country of the Dominican Republic. I mean, naturally I was both excited and nervous. I think mainly because we had not met in person. He actually flew into Chicago and we first met in a lounge at the airport. When we met he actually seemed a little more nervous than I was, which actually made me feel better. The conversation went well and we both talked non-stop all the way down to the Dominican Republic.

Once we got to our resort, I have to admit I was just blown away at the absolute beauty of the place. It was far nicer than the pictures I had seen online.

After a complimentary drink at reception we went to our room to unpack. The room was great, but kind of small… not that I was complaining. We decided to unpack and change and then head to the beach! He actually went and sat in the washroom to allow me privacy while I got changed. It actually surprised me.

But this is where things took an interesting change. When we got to the beach he asked me almost immediately why I had agreed to travel with him given he was so much older. He actually pointed out some of the young men on the beach and said wouldn’t you rather be with one of them? I told him no, and that I was attracted to his personality. But he was persistent and said he knew he could not offer me the sexual satisfaction that one of the younger men at the beach could offer me. He then said that he didn’t have any expectation of having sex with me while on vacation. It was not what I was expecting at all. But then things continued. He told me that he wanted me to have sex while on vacation and that he would not stand in the way of this. In fact, he said he would really desire for me to pick up a man or different men, and then bring them to our room and have sex in front of him while he simply sat and watched. He actually insisted on this and said it was his true desire and his biggest turn on.

Now, I am an outgoing woman, but I am not the type to go and pick up strange men. So I wasn’t exactly sure about his suggestion. I mean, I couldn’t see myself just picking up a man and having sex with him, let alone while my Sugar Daddy watched. But later at dinner he kept persisting and said that I should not deny myself the pleasure of great sex while on vacation at such a great resort. He also said he knew it was not my style to just casually pick up a man, but that it would turn us both on. So with a little bit of wine courage in me I agreed.

We started looking at the different men at the restaurant and he started picking out men for me. It was a little embarrassing at first, but then he asked me to pick my choice!! So I saw a man that I could tell was in his early 20s and suggested that he was my type of man. Almost instantly, my Sugar Daddy sent over a bottle of wine to his table who was dining with another man and woman. The man came over to thank us both for the kind gesture and introduced himself to both of us. His name was Randy and he was from Portland. My Sugar Daddy didn’t mince his words and said, “my friend here has been looking at you and told me that she has a desire to have sex with you. Would you like to have sex with her?” Talk about my jaw dropping to the floor! I couldn’t believe he said that. Randy was also caught off guard, but his smile instantly lit up and said that he had never been approached by a lady like this and had never been asked if he would like to have sex. I could feel myself turning all kinds of colors of red at this point, but at the same time this conversation was beginning to turn me on.

So then my Sugar Daddy said, “well I think it is settled then. Why don’t you join us in our room after dinner and you can have sex?” Randy asked for our room number and said he would see me in about an hour. So off he went back to his table and that was that.

Back to the room we went and I admit to being quite nervous. After about 20 minutes there was a knock on the door. This time Randy brought a bottle of wine with him to return the favor. My Sugar Daddy welcomed him in and cracked open the wine. Then he told Randy what was in store. He told him that I was his for the night, but that the only thing was he would be in the room the whole time watching as we had sex.

Maybe it’s a guy thing, but Randy seemed to have no problem with this at all. So with that we dimmed the lights and we had sex. I will just say that I chose well. We had great sex and went on throughout the night. The whole time my Sugar Daddy sat in a chair and watched. I watched him too, and I could just see the enjoyment he was getting watching me have sex with this strange guy whom we sort of picked up together. I remember having such a rush with him watching us. I thought it would be weird, but it was so amazing. The only time he spoke was when I was having one my many orgasms. He simply spoke out and said, “don’t hold back.” This was such a turn on, and I didn’t hold back.

As for Randy, I think he was quite happy. This I learned later was called a ‘cuckold’ experience, and I have to tell you it was the hottest sex I have ever had. We didn’t pick up any other men the whole week, as Randy became my sex friend for the week and we actually all hung out at the resort together. At night, it was always back to our room with my Sugar Daddy watching while I had the best sex of my life.

This type of experience may not be for everyone, but it was a side of sex I had never experienced before and for me it was something I really enjoyed.

So much that my profile has now changed and I outwardly state that I enjoy cuckolding. What is even more cool is the amount of other men who are really into this type of experience. I personally loved the empowerment of picking my sex partner and not being judged for it.

What an amazing experience I had in the Dominican Republic! I’ll never forget it.


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