First Time Secrets

Jeanette wrote in recently with three questions I get asked a lot, so here’s a triple shot for all of you where I’ll answer all three questions!

Here’s the first part of Jeanette’s email:

Hi Samantha,

I am in my teen years. I met this guy about 8-9 months ago. Well, I fell in love.

I’ve been thinking about it a lot because I’m still a virgin and I want to lose my virginity to him but at the same time I’ve never regret anything in my life and I want to keep it that way.

1. Is the missionary position really the best way to lose your virginity?

Jeanette, for almost everyone out there, missionary or girl on top are the two most comfortable positions for your first time. The thing is to know yourself and know which position you would feel the most relaxed in.

With girl on top you have more control –  you’re in charge of when he enters you, how quickly or slowly he moves in and out of you, and so on. Some guys will instinctively start thrusting away, though, so make sure to let him know you’ll do the moving until you’re used to the sensations and you’re ready to let him start playing along.

The missionary position may be for you if you’re worried that you’ll find it hard to relax. (In girl on top, your muscles are engaged in keeping you sitting up and straddling. The key here is to have a partner you trust to be gentle and considerate, and not just try to “stick it in.”

Of course, both the positions I’ve described should only come AFTER you’ve done all the basic preparation. You’ve addressed any issues with your emotional health and safety; you’ve learned how to prevent sexually transmitted infections and unplanned pregnancy; you’ve both learned how to get your partner aroused and comfortable so the sex will be great and not awkward or painful.

2. Me & my boyfriend have been on and off for the past 8 months. I love him and I know he loves me but he has cheated on me. Since that happened I dont have as much trust in him, but at the same time he’s been the sweetest guy in the entire world. If I lost it to him do you think I would regret it?

In the end, you’re the one who probably knows the answer to this, deep down in your heart. I don’t know you and I don’t know your boyfriend — but I do know that he has cheated on you.

You mention that he’s sweet, but I’d say this doesn’t make up for his past infidelity. Did you find out about his cheating and confront him about it, or did he confess independently? If he confessed to you, that might indicate that he understands his mistake, and is capable of acting trustworthy in the future. If he didn’t confess and you had to confront him about it, well, I’d say there’s no evidence you can trust him now. Trust can be rebuilt after it has been broken, but that doesn’t happen overnight.

Trust is absolutely the most important thing in a sexual relationship. Sex can hurt you emotionally AND physically; it can give you a disease or result in an unwanted pregnancy. And bad sex can make you miserable. A lot of adults are in therapy for bad sex they had when they were young. But good, safe (use a condom!) sex is wonderful!

You need to be able to trust that your partner will honor and respect you and your body. When he cheated on you, he could have caught herpes just by making out. If he had unprotected sex, he could have caught any of a number of serious STIs that you might now be exposed to.

In the end, it’s your call, but I only recommend having sex with someone you KNOW you can trust. If you are having trust issues, you may find it hard to relax and enjoy sex. Your body will react to what is going on in your head.

Good luck with this decision — it’s an extremely difficult one. If you feel like you need more advice on this, my book does cover the topic in much more detail.

3. If I’m scared does that mean I’m not ready?

It could - or it could mean that he is not the right person for you to be losing it with. Sometimes fear is a natural reaction to a new situation, and at other times, it’s our mind’s way of telling us that we’re making a decision we don’t actually believe is the right one.

I have included an “Am I ready” checklist in my book which I think you find really helpful. Losing your virginity and embarking on a sexual journey will open up a new stage in your life. You are smart to be asking these questions and giving it the care and consideration it deserves.

Doing things for the right reasons is how you have managed to avoid regret this far in your life. Now you just have to figure out what the right reasons are for losing your virginity. I wish you all the best.

For the rest of you reading this, if you’ve got the same questions and more, my book is a safe, fun guide to everything you need to know to have great sex for the first time — check it out!

To great first times,

Samantha