First off just know that long distance relationships can be both rewarding and frustrating. I'm sure already you have had feelings of wishing he lived closer. Maybe in some ways you also might glad he's not here because he could distract you from other things. As far as this first meeting, yes it is your first date.
These days because of the technology we have available to us, it can make things more confusing as to getting to know each other. We think because of the texting, and the emailing or even phone calls that you are really getting to know each other. There is also something to be said about being with and around someone else's energy. The in person time is the most important. How much in person time someone is willing to and actually makes the time to spend with you speaks volumes. I know because of distance that could make it a big difficult.
You two have so much to learn about each other and possibly from each other. The biggest mistake you could make is rushing it. A good question you can ask yourself is what am I supposed to learn from him by attracting this man into my life? If you are already feeling unsure about sleeping with him then let that feed into your decision. If you were sure about it and you knew that after sleeping with him, no matter what the outcome after you left, then if you feel like you want to then go for it.
Also keep in mind that we have a chemical in our body called oxytocin that when we have sex with a man it gets released in our body that encourages us to "bond" and want to "pair" with him. It also sounds to me like that on some level you may have already decided that he is your next "the one"? I am making this assumption based on your comment about waiting a few more trips assuming there will be more.
Also do you know what his future vision is for himself is? Is he just getting back out there in the dating world too or is he looking for his next wife? If you were just looking to have fun and get out there yourself, I don't think you would be concerned about when is the right time to have sex with him. If this is your first dating encounter it might be best to take your time so you can really get to know yourself in the dating world again, such as getting to know what it is that you value in terms of relationship and then slowly see if he is a good fit for you.
I hope this helps. If you want to chat more about it feel free to email me at email@example.com.
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