I received the following question on Formspring last week:

Hey City Girl!! I wanted your advice on losing one's virginity. How do you know when the time is right? I have an amazing bf but am still worried about my first time and don't want it to be a bad experience. Any advice?

Here are my thoughts:

The short answer to your question is that I can't tell you whether to lose your virginity or not. That's a decision for you and your boyfriend to make. (I've said the same thing when readers ask me about trying anal, a threesome or having sex shortly after ending a serious relationship.)

With that disclaimer, there are definitely factors to consider as you make your decision. Here are a few that come to my mind:

1. Why have you waited up until this point? If your interest in losing your virginity is based on pressure that you feel from your boyfriend or friends who have already had sex, then you might want to wait to be sure that the decision is yours and yours alone. If you've waited until your relationship has reached a certain milestone (three months of dating or an engagement ring, for example), then have you reached that milestone? If so, do you still feel the same?

2. What expectations do you have about your first time? I loved my high school boyfriend, Boston Christian, with all my heart. I've never regretted losing my virginity to him for a second, but the act was also incredibly painful. Sharing that experience together was wonderful because we loved each other as much as two teenagers can, but the sex wasn't.

Are you close enough as a couple that you could make it past a bad experience? Would you be okay if it doesn't turn out perfectly? What are your expectations of losing your virginity? Are you both on the same page in terms of how you feel about each other so that adding sex to the mix won't complicate things?

3. Have you discussed all the possible ramifications of pregnancy, STDs and AIDS with your boyfriend? If you don't feel comfortable talking about these topics with him, then I would question whether you are ready to have sex. Are these issues easy to bring up? No. But, they are necessary. Are you both going to be in a sexually-monogamous relationship? Will he be wearing a condom? Are you on birth control? Has he been with anyone before you? If so, do you want him to get tested first?

I addressed some similar issues in last month's post about: How soon is too soon to have sex with a new guy? Determining relationship expectations and discussing birth control and STD/HIV testing need to happen whether it's your first sexual partner or your 50th.

Please take this post as friendly advice, rather than encouragement or discouragement. If you read through this and decide that you're ready, then you are! But, if the post raises more questions for you than answers, then you might prefer to wait. You can always decide at a later point that you're ready. There's no right or wrong so just follow your heart, use your head and be safe! xoxo

Readers: What would you recommend? How was your first time?