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Dr. Betty,

I'm 18 years old, and last night a friend and I tried to have sex. I have never had penetrative sex before, but he has been with several different girls, although never with a virgin before. I had also never been penetrated with anything at all, including my own fingers, so I wasn't
sure what to expect.

He tried to enter me and all I felt was a kind of pressure, and it didn't feel right. I told him that I wasn't sure if it was working, and he suggested that he finger me first, so we tried this but it still felt uncomfortable and - I don't know how else to describe it - it just felt wrong. I told him this, and he said I should try fingering myself because I have smaller fingers than he, but when I tried this I got the same result. After a while of this, he concluded that I would just need to do it the first time myself.

My questions are - is it possible that we were doing something wrong? I know what is supposed to happen in theory, but not in practice, so I am not sure. The other thing is, how should I go about "taking my own virginity", and what exactly would this mean? I don't feel comfortable using my fingers because it doesn't feel right, but will this get better with time and practice? Should I try with a toy of some kind? This is the part that worries me the most, because I'm afraid of hurting myself, and I have a very low pain tolerance. I also don't know where to purchase such a toy, and most of them look quite intimidating.

I would really appreciate advice on what to do about this, as I am a very sexual person and I am looking forward to enjoying penetrative sex as well.

Dear F,

First check out the categories along the left side of our website. Go to First Time Penetration. Start reading the Q & A that are there. Take your time. Now for your questions:

Is it possible that we were doing something wrong?

Most likely yes since neither of you know what to expect or what to do.

The other thing is, how should I go about "taking my own virginity",

My answer is YES, take your own virginity. My first question for you is, are you able to have orgasm during masturbation? If not, that's the first place to start. If you are unable to purchase my vaginal Barbell, at least read the instructions and get in touch with your pelvic floor muscle so you can focus on relaxing it. Using your finger would be best at first. Later on you can carve a zucchinni or carrot down to size.

After stimulating your clitoris for a while, begin to SLOWLY ease your finger inside while squeezing and releasing the muscle. Breathe into the feeling of discomfort like you were giving birth. Eventually you will get over those feelings of being so uncomfortable. As for hurting yourself, that would require developing some trust in yourself and knowing that you can stop at any point. 

The most important aspect would be getting yourself very sexually aroused before using your fingers or a dildo. Go to "First Time Orgasm" and read my step by step suggestions. Get to know your vulva. It's best to own it before you share it. Make sure to have plenty of lubrication like my Almond oil or some other massage oil that doesn't have perfume or chemicals in it.

Now go have a Happy Orgasmic New Year.

Dr. Betty