Scarleteen

A boy that I have known for a year now could have been my first real boyfriend but I wasn't ready for something like that yet. We almost had sex a few months ago but I was embarrassed and couldn't do it and he was okay with me waiting for the right time.
A couple weeks ago I was with some friends and I had sex with one of the boys in the group, I was more comfortable with not knowing him and us not having contact after we did it. I didn't plan on having sex but we got to know each other and I was okay with doing it, I am still surprised that I went that far.
Yesterday I was back with the boy I have known all this time and I would like to now have him as a boyfriend and have sex with him, but I haven't told him that I already did it with another. He is a virgin but I am no longer one but we both wanted to do it and lose it together.
Do I tell him or do I not? I'm torn on this. I don't want to hurt him with the truth, I also don't want to hurt him later if he somehow finds out.

Hi Polkie, welcome to the boards!

It’s very understandable that you would feel more comfortable trying partnered sex with someone you know you would not see again. It might not be for everyone, but I can see how it would make this less intimidating, and it is a perfectly reasonable choice. When you say you were okay it sounds like it went well, but I do want to check in: since you are surprised you went that far, do you still feel good about what happened?

Yesterday I was back with the boy I have known all this time…

If you are interested in a relationship with with this boy, I think it would be a good idea to tell him about what has changed, just so he doesn’t have the wrong impression. I imagine you don’t want to make him feel bad, but at that point, his feelings are his responsibility. You may have talked about trying partnered sex for the first time together, but that doesn’t mean you had any real obligation to do so.

How does this sound to you? Are you worried that he might not want a relationship with you if he finds out about this?

Surprised because I wasn't thinking about it, and surprised that I did it with him. I was at a pool party with friends and the boy who approached me lived there. Less intimidating because everything with him was so fast, he was not a virgin and he just wanted to do it. He did ask, it wasn't any pressure.

I might tell him. I hope he still wants to do it after I say something, at least I wont be so worried this time around. Would like to have him as a boyfriend but I don't want him thinking that he has to be better than the other one. I think his feelings will be hurt and that will be the end of it.

Honesty when it comes to sex (and relationships) is very important. Lying about this to him wouldn't set a good tone for the beginning of a relationship, either. There's a chance he will appreciate the honesty and respect your decision. Do you want some help brainstorming how to approach this conversation with him?

it happened.
Not what I thought it would be like.
Told him about me being with another guy. He wasn't happy about it, wanted to know why I never wanted to do it with him, and we had many times where we could have but I didnt feel ready.
After 10 minutes of talking about the WHY he asked if we could have sex.
I feel used now. Like all he wanted was sex now that he was a bit pissed of me already doing it.
So yea we had sex. I got nothing out of it. I don't think we have any relatonship after this.
I know I hurt him. I wish I didn't wait so long on doing it with him, I think it would have been better if I was with him first and not be so pushed into doing just because I did it. Does that make any sense?
And he still hasnt texted me. It's like he doesn't care, causing me pain in return.

Hi there, Polkie

It makes a lot of sense that you wish you didn’t feel compelled to have sex with this guy. Even outside a relationship, it’s fair to expect to feel cared for as a person when you have sex with someone, and any sex should be freely wanted by all involved. It is clear that this wasn’t an emotionally supportive, positive experience for you, and it is concerning to me that you’ve been left feeling so bad.

As I said in my last response, you didn’t owe him sex or your first time, even if you discussed the idea. It’s one thing for him have his own feelings about what you told him, but it is another for him to be angry with you and to be inconsiderate of your needs. It isn’t okay for him to intentionally hurt you just because he felt bad. I know it can be deeply painful to be treated with indifference and anger by someone you’ve been close to, but he is acting in ways that are not okay for a friend or a partner right now. Does that make sense?