Scarleteen

I have a friend who is gay, he is 16, and we have been friends for 5 years now. We have always been a bit open about our sex lives with each other, I was always curious about his gay partners, and he was curious about my straight ones. I would find his type of guys attractive, and he would find my type of guys attractive as well.
He is also a crossdresser but it's in secret, but he does trust me with it and I have seen photos, I have even given him some of my clothing. He is on a lgbtq teen site and he has posted photos of himself, just not showing his face. He gets great reviews, lol
My confusion is this. We had sex together just a few weeks ago. He asked if he could which was a surprise, I never looked at him as a partner. He wanted to experiment and see what it was like, and he was honest about it and just wanted to try it. He didn't seem all that interested when we did it, and I was a bit uncomfortable with it as this is just a friendship and nothing more, but we did have fun and laugh about it.
We have been texting the last few days and he wants to do it again, but this time dressed as a girl. I haven't' really givin him an answer, been a bit quite about it, and now he has apologized and I feel like he is mad at himself for asking.
I think he wants to be trans, or maybe a secret trans. But why does we want to be having sex with a female now? And I am straight, I am not bi, but now I am having sex somebody who is gay and maybe trans, so am I now BI curious?
How should I talk with him about this? And should I give this a try? And do I have sex with him as a boy or do I have sex with him as a girl?
I am not being judgmental here, but I am lost on how to do this, but I am curious myself.

Hi gizmoX,

Welcome to the boards! I want to start by saying that sexuality can be fluid, so from what I'm hearing, your friend is exploring their sexuality and identity. That said, we cannot tell you what to do or what not to do since we don't fully know your comfort level here. Are you feeling obligated to continue a sexual relationship with your friend? It would help if you could expand on your feelings more.

Additionally, we can't identify your sexuality for you. However, we can provide resources that could help you find some terminology that best fits how you're feeling about yourself. I'll link it here: The Rainbow Connection: Orientation for Everyone.

Lastly, I think the best thing to do here is to communicate exactly how you're feeling. You should not overstep your boundaries if you feel uncomfortable continuing to have a sexual relationship with your friend. From what you've been telling us, your friend seems to care about you and worries that they might have overstepped. I recommend that you clarify how you're feeling about this so there is understanding on both sides! Again, we cannot tell you what to do here, as this is entirely based on your comfort level!

Please let me know if any of this helps and take care!

Hi gizmoX,

I just wanted to chime in with a few additional points!

When it comes to the actual conversations, I think a good first step would be to have a check-in where you both have space to say how you're feeling about this whole thing. That could include what parts of it you're comfortable with and what parts you feel confused or unsure about. I think, given the fact you two seem to be pretty close friends, you could ask him if he feels like this is helping him explore his sexual orientation more. I really like this tool for having those kinds of conversations: Be a Blabbermouth! The Whats, Whys and Hows of Talking About Sex With a Partner

As far as the gender stuff goes, it's possible he's trans or nonbinary, but it's also possible that he just enjoys dressing up in those clothes for another reason. Only he can really tell you the answer there. What might be helpful is to think about whether you'd be comfortable being sexual with him if those clothes were part of it, or if wearing them meant he wanted to introduce a certain dynamic into sex. Because if you're not comfortable with it, then that gives you your answer about whether or not to do it, you know?

Thanks for the replies. I am very happy that I found this place

I don't know what my comfort level is. As for my boundaries that is a line that has changed quite a bit these last 9 months. He is my best friend, I like him for who he is, but he is not my type and I don't find him sexually attractive (although he is very adorable and super funny). My mom likes him enough that he is even allowed in my bedroom, although it's probably because she knows that nothing would happen between us.

We have a close enough "friends" relationship that I went right to him right after I lost my virginity, and I had no problem crying with him and talking about it. I like the relationship that we have because he is different, he is not the normal boy in class, and I love him for it.

The sex we had a couple week ago was extremely basic penis/vagina stuff, no foreplay and no kissing and he didn't even want to see me naked. He was just curious and wanted to know what it was like. I did not feel obligated to do it, I found it funny that he asked, and I had no problem doing it with him, but I was thinking it was just a one time thing.

I think what I want to do is try it and see, but we are going to have a big talk about this before we do it! I guess he is curious and I am curious just as much but for different reasons? Or maybe I am just curious because he is?

I still don't understand why he is becoming somebody else with me, that is the one big question I have. I don't understand what he wants out of this, that is my other big question. Isn't he asking me to somewhat change my sexual orientation? Or maybe I could say that this is just fun and games between us and nothing more?

Should I ask him if he wants to be nonbinary? And how does that work? Is he a guy who likes guys one time and a guy that now likes girls the next? Or should I call him a they and let him see if they likes to be with a girl? But am I a nonbinary when I has sex with him? I am laughing with confusion btw, lol!

I did text him back and told him that we can talk about this and see what happens. I don't want to be in a rush about something like this.

Hey there, gizmox.

So, I don't think that it's sound to ask someone if they want to be a given gender identity. For one, that's just not really someone else's place -- it's for any of us to get a sense of our own gender identities, not really for someone else to offer it up like that, you know? Gender identity, as you may know from your own, is something felt (or not): if your friend feels like they are a nonbinary person, and that's something they want to share with you, or that feels like it has something to do with their relationship with you, they'll let you know.

Too, though, I think it's important to remember that gender doesn't = orientation. These are actually two different things, even though they can, and often do, have to do with one another in some ways for many people.

For sure, for those of us who are nonbinary, binary frameworks like gay or straight won't really tend to work, because they ask us to be or think about gender in ways that aren't usually a match for us. But there are also nonbinary people who don't feel at odds with those frameworks at all.

What I am hearing here in your posts isn't that this is a person changing who they are, but that this is a curious person who is exploring and experimenting, maybe to find out more about who they are. (Sounds like maybe that might also be the case for you with this, too?) I don't see that this is someone asking you to change your sexual orientation.

Sexual orientation isn't what we do, it's about what we feel and how we choose to identify that: in other words, it's about how we feel attraction, whether or not we ever do anything with those feelings, and even if what we do seems or is clearly at odds with that identity. But by all means, if what your friend wants feels outside what you want to do for yourself, or isn't something you feel comfortable with, or is at odds with who you are in a way that doesn't feel good to you, you get to nix that, always, anytime.

I'm not really getting a sense of what YOU want, for yourself in any of this. I hear that you don't feel obligated. I hear that you don't have a problem. But those things don't tell me what you actually want, for yourself. What do you want, for you? Do you want to be sexual with this person for yourself, separate from what they want?

Hey, heather. I did read your reply las week but wasn't sure what to say.

I had a chat with him, only had a few questions but I did tell him my boundaries. I love how he is curious about all of this but I did tell him where my line is at on what we do together. Everything is good between us, and whatever he says or does is no prob with me. He is already back to seeing this new boy, which takes me off the hook a bit

I am okay with being sexual with him. I like the playfulness of him, plus he is not shy on saying what he wants. I had one partner a year ago that was so scared that he would talk himself out of it.

Thanks again for all of the info.

Hi!

I’m so glad to hear that everything is working out. Please let us know if you need any further assistance!