Dear Sasha, I’m 16, and I was raised by a great single mother. My mom and I are very close, she had me when she was young, and my father left us not too long after I was born... anyway, my mom’s always been very open with me about sex, and she’s made me promise her to wait until I was 18. I always meant to keep that promise, but my boyfriend and I have been dating for almost 8 months now, and it just kind of happened a couple weeks ago... it really was nothing like I thought it’d be, as in it didn’t last long at all, and it was super uncomfortable, but we were safe and used a condom and everything. Now that we’ve done it, my boyfriend wants us to do it more often, but it really wasn’t that great, and I broke the promise I made to my mom, so I told him I want to wait until I’m 18. I feel really guilty about lying to my mom, and sometimes she says things that make me feel like she knows what happened... should I tell my mom I had sex? Even though I know that I broke her trust, and she might be really pissed at me? thanks L  

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I’m sure I don’t have to tell you L, because you know better than anyone right now - there is immense pressure surrounding the first-time cherry pop. Not only has it been built up to be this life-changing event, but you also have to worry about everyone's perception of you -- i.e. what will your mom think, did your boyfriend like it, what will your friends say.....

So before we go any further L, I just want to make sure you’re happy with your decision and that you didn't feel pressured to do anything that you didn't want to do. And listen, just because you did the deed with your boyfriend doesn't mean you have to continue doing it. If you want to take a little time out and wrap your head around things, then that’s totally cool. Take that time. On the flipside, if you’re still curious to see if it gets better and it does, there’s no shame in that either. Basically what I'm saying is do what feels right for you.

Now let’s get to your mom. If the overarching bad feeling in all of this is the guilt of breaking the promise to your mom, well, then her trick worked. I say trick in the most loving way. While she may have hoped you’d wait until you were 18, I think that pact between the two of you was less to do with what age you’d lose your virginity and more to do with just being honest and open with her. So L, if you want to alleviate some of this guilt then just sit down and have the discussion with her. Sure, it will be a bit uncomfortable and yes, she might play the disappointment card, but trust me, in time she’ll relax and in the end she’ll be happy that you told her.

Keep me posted and let me know how it all pans out! xx