Dear Panel,

I am a teenager. I'm Intelligent, affectionate, quiet and typically loyal.

Mary is sweet, like the epitome of sweetness. Never a harsh word or action. She always smiles, is sweet and caring and understanding. She's typically quiet, affectionate, cuddly. Too good for a guy like me and what I did to her.

The other person is Caitlin. She's kinky and all in all I just don't know much about her.

She Isn't Interested In Sex

I met Mary about 6 months ago . We became an item about 3 months ago. She's a good girl, who has to be coaxed to progress physically. Being quiet, sometimes I feel distanced from her.

Anyway, about 2 weeks ago, I was very seriously considering breaking the whole thing off because we weren't connecting both mentally and physically. During that time I began to talk to one of her friends, Caitlin, and we often talked about things of a sexual nature--we're teenagers.

I Had Sex With Her Friend

To make a long story short, we agreed to go out, and she was going to show me the ropes of handling the vagina. Once again I'd like to reiterate, I'm a teenager.

I agreed, and so we met up and we got going. Basically this was for me, so that I can learn how to get the stuff to work, so I can be good for Mary if she were to ever let me. One thing lead to another, and I ended up inserting my penis in her vagina, instead of my fingers.

I'm trying to tell myself that I didn't loose my virginity, because it was just for a short while, but I don't know.

I feel absolutely destroyed by the whole thing. If I were to tell Mary about it, we may break up, and I don't want that. If I don't tell her, this whole thing will blow over, as neither I nor Caitlin will tell her about it.

Should I tell Mary about what happened?

Male, age 16, USA

William, Morticia, and Indigo answer this question.