Is This a Terrible Thing to Do?

I'll try and keep this from being a wall of text. Im bisexual and extremely lonely. Im a virgin and have wanted to lose my virginity for a while now. There is a guy that was very in to me but I was a lot less comfortable with myself. I never found him very good looking(he is overweight by quite a bit), but was intoxicated with him as a person. I havent spoken with him for a while, but have been very tempted to recconnectOnto the question.. I want to message him and see if things go forward. He is someone im truly comfortable with the idea of having sex with. The problem is that I dont know if I see a long term relationship with him and I dont want to make contact with him if I may hurt him. Would it be bad to contact him, knowing that I may only want a fling? Id be extremely upfront with him, but i dont want to hurt him at all by messaging him and giving him the wrong idea before we met.