Hi Sarah, thanks for contacting Alterheros with your question!
There are a few different issues to address within your question, so lets take a look at each one separately.
First, you and your male friend are both virgins and want to have sex together for the first time. There seems to be a lot of different emotions involved for each of you. You seem to really love each other and have each others best interests at heart. But, you’ve also said that he feels jealous about you being with other guys and is threatening to be hurt and upset with you if you just go and lose your virginity to someone else. But wouldn’t that be your choice? It’s not very fair of him to be pressuring you to save your virginity for him. Nobody has a right to do that to you, regardless of how much you trust them.
Another thing to consider is: do you think you’ll be able to stop having sex with your friend after the first time? What if you don’t stop, what if you keep having sex, and then one of you wants to get involved with someone else? Since he is already jealous of you with other guys sometimes, how do you think he would react if after having sex with him you started dating or having sex with someone else?
I would advise the two of you to sit down and discuss this for real. Discuss all the options, feelings, possible outcomes, and even some rules and guidelines. Define your relationship and the expectations both of you have. Make sure that you are both on the same page. Also, be sure that you aren’t doing this in order to keep him as a friend. All of this will help to strengthen and protect your relationship.
Second, you say you are scared to turn him gay. Relax. Although it depends on what your beliefs are, it is generally assumed that you cannot turn someone gay. Homosexuality is something humans are or are not born with, not something that happens because they had sex with someone of another gender. Now, it is quite possible that having sex with you (a woman) your male friend will learn more about himself and his sexuality. That’s what this is about, exploring your sexualities together. His exploration may lead him to discover he is gay, still bisexual, or completely straight. Who knows. But, no matter what, you cannot turn someone gay. It just doesn’t work that way.
Regardless of what you decide (there is no right or easy answer!) be sure to use a condom for every sexual act (oral, vaginal, or anal) that you might have. Just because he’s your friend and you trust each other, doesn’t mean you don’t have to be just as safe as everyone else.
Feel free to look at a similar question that was asked recently, maybe that answer will help you some more: https://alterheros.com/english/ask_experts/ask.cfm?QID=995
Hillary, for Alterheros.