Scarleteen

Not sure how I should ask this but a reply would be nice.
I had sex with a friend in January. I did it with him because I was curious and because I trusted him. We talked openly about sex and relationships previously but I never expected on actually having sex with him. I had sex with him one other time in February, I was still comfortable with him, but after that I just wanted to be friends. I didn't want sex to hurt a wonderful friendship. I never told him this, but he never did ask if we could have sex again, so I felt like everything was back to normal between us.
Last few months have been nothing but isolation. Found this new boy online, become good friends, and we met in person just a few weeks ago. the STUPID part of me is that I went to his house knowing he was home alone and I had sex with him. I already had it in me head on doing it with him, but I didn't want to just jump in bed with him either! I should have met him at the park or something.
The OTHER STUPID thing is that I told my friend this, the boy who I first had sex with. BTW they don't know each other. But I told him how sex wasn't all that great with this NEW boy, and I told him on how I preferred having sex with him instead. I said it in a funny sarcastic way, nothing serious, but he took it like some kind of GREEN LIGHT and he started asking if we could have sex again. Now nothing happened that day, I laughed it off, but a couple days later I had sex with him, and I did this because I like him and he is a good friend and I am comfortable with him.
This Saturday I am AGAIN going out with boy number 2. I am going out with him because I find him funny and attractive and I would like having a relationship with him. My friend (boy number 1) is a good friend and I want to keep the friendship, I don't want it to be a sexual relationship. But like I said in the title how do I fix this? Should I tell this new boy about the boy I have a friendship with or should I just not say anything? I already intend on not talking with my friend about my sexual life anymore, and I already intend on not having sex with another boy while in a relationship EVER AGAIN, but should I be honest and tell this new boy the truth or should I just move on?

Hi ThatGirl,

I think there are a few conversations to have to help you sort this all out. The first one is with your friend. If you want this friendship to stay non-sexual going forward, then having a conversation where you explicitly say that is the way to make sure you and he are on the same page about your expectations for each other. Does that feel like a conversation you can have and a boundary you can hold?

With the new boy, I think mentioning that you've had sex in the past is part of a slightly different conversation, one where you and he are talking about your sexual histories as part of figuring out what you each need to be safe. I don't think you necessarily need to go into the details of what happened with your friend with the new boy, unless you and the new boy had already agreed to be exclusive.

You might also find this article helpful when it comes to figuring out and holding whatever boundaries you need to around sex with both of these guys: When Sex "Just Happened" (And How to Make It Happen Instead)

I wasn't entirely sure if I should tell this new boy in my life what I had going on with my friend, I would prefer keeping that to myself. The weird part for me was having sex with the both of them just weeks apart, but from here on I want to only be with the new boy, at least for now. And I had that conversation with my friend just a few hours ago. thanks

You're welcome! Did the conversation go okay?