Scarleteen

For context, I’m in a sort-of-polycule with two friends. I’m a trans guy (15) and the members are another trans guy and a trans girl, both also 15. I’ve gone to second base with an ex once (another trans dude, we fingered each other for like 2 minutes and it sucked) but nothing more.
Both the other members are 90% likely to visit my hometown in 11 days and will be sleeping over at mine, as soon as one final parent confirms. We half-joked-but-not-really about one of them bringing a strap-on, which both of them have, as it’s been a longtime fantasy of mine to wear one and I think they both like the idea.
The problem is I don’t really know how it’ll work. I don’t even know if it’ll happen. I’m planning on buying condoms and lube just in case, but I’m scared of getting my hopes up. Multiple times we’ve mentioned bringing a strap, but idk if it’s a joke and the polycule itself was started as a bit of a joke but not really, and I think we’re all sort of hesitant to make the first move romantically or sexually but I could be wrong. I think I’m getting in over my head.
If we were to have sex, after talking about boundaries, what the heck will happen next? Who will do what? I’m not even sure if I’ve experienced an orgasm before. I know one of them has performed oral and the other lost her virginity at a young age to an abuser, so idk how experienced we’d all be with each other. I think I’m rambling now, I just have no idea wtf will happen or what I’ll do. Will I be dominant? Submissive? A top or bottom? Will I be doing oral? Will I be penetrated? I think I know what I want, but not what they want. I don’t even know if it’ll happen.
God, please help me figure this mess out.

Hi transdude_art and welcome to the boards!

I think there are a few parts to your question here so I'm gonna break it down!

Firstly, It sound like you are a little uncertain of you own wants or desires. Have you thought about what it is you want or don't want? Both sexually but also within these relationships?

We have a great article which talks through 'readiness' for partnered sex that I think could be helpful for you - Ready or Not? The Scarleteen Sex Readiness Checklist

Communication is the key to any and all relationships. It sounds to me like discussing some of your worries and also wants with your partners needs to happen prior to any sex. Communication becomes even more vital with more people, so it is important all three of you are on the same page!

Here is a great article on building that communication foundation -- Hello, Sailor! How to Build, Board and Navigate a Healthy Relationship.

You also mention worries about what would actually happen if you were to have partnered sex. That can partially be solved by communicating once again! It may be beneficial to go over a check-list, like this one Yes, No, Maybe So: A Sexual Inventory Stocklist, about sexual wants.

There will be lots of 'new' with a first sexual experience. It may be worth checking-out this article which goes over some of that 'new', The Sex Goddess Blues: Are You Ready For Partnered Sex?.

I also would like to add that being worried like this is normal because it is a BIG jump to make from what sounds like infrequent contact to intercourse, especially at your age. Sex should come from sexual desire which often takes some time to build between people. That speed depends on the person, but it is important that all people are in the same place prior to doing anything further. Sexual acts should be something you are desiring, not something you are worried about happening. Does that make sense?

It might be worth seeing how those sexual jokes or comments are really making you feel. If it is worry and stress, it is worth asking your friends to tone it down or place some boundaries there.

Thank you so much! I’ve read these all and they’ve helped quite a bit. I think I’ll try to jot down what I want and put it out of my mind u til they get here and we can talk. Thanks again!

And you might not even know what you want until you actually spend some more -- or any? I'm not sure I understand if you have ever met either of these folks or not in person -- time with either or both of these people.

Something like strapping on would be a whole lot for anyone the very first time they are with a partner, even people older than you with a good deal of sexual experience, including with that activity, under their belts. I think you feel in over your head because you are in over your head. I think doing some of what you're talking about would be like throwing someone into a pool who doesn't even know if they can swim yet.

The first time you really spend time together is probably one best spent doing a lot of talking and even just seeing what your chemistry is like and how you actually feel about each other, to start. If you've never actually met, it may even be that one or more of you finds out you don't even have sexual feelings for the other, you know?

Thank you, I think I am over my head a bit. We spent about 2 and a half weeks in the same bunk at camp, so we bonded a lot and have really gotten to know each other. That being said, I don’t think we know each other to the point of full penetration out of nowhere.
I think I’ll wait to talk to them to figure it out, and still make sure to get condoms and such just in case, as I think I’m ready for sexual activity if they’d like that.
Thank you all again, you’ve really helped me. <3

For sure, any kind of intercourse (I don't personally use "penetration" as an educator to talk about any kind of sex because it gives people wrong ideas about how orifices work -- which often means people engaging in things like vaginal or anal intercourse or fingering in ways more likely to hurt than feel good for the receptive partner -- and also better describes sexual assault than anything wanted and consensual) sounds like it would be very much out of nowhere at this stage.

If it helps, I'd say that before anyone thinks about doing anything like that, they'd want to have at least done things like seeing if they even enjoy touching each other -- like with cuddles, kissing, touching body parts over clothes -- and if they even feel comfortable being vulnerable in the ways sex of any kind has us, like how you felt being naked together, for instance. And absolutely, real talk -- so much real talking.

So glad we could be of help! I hope that no matter how you spend them together, these are wonderful visits for you!

Thank you!!