First Sexual Encounter

By December 27, 2017December 29th, 2017No Comments

I am a 15 year old male who discovered several years ago that I prefer to wear girl’s clothing including panties, dresses and skirts. As time has gone by, I have spent more time in girl’s clothing instead of dressing as a boy. I never thought of it as a sexual thing, I just liked the way it felt.  I have learned to live with the remarks and stares because I am comfortable in the way I dress.  Two months ago, I was at my best friend’s house working on a school project. As usual, I was in a dress. I was leaning over the table when I felt him come up behind me and start rubbing against me.  I know I should have told him to stop, but it felt kind of good. I finally told him if he wanted to go for it, it was okay.  I really enjoyed it. Later that night I decided to preform oral sex on him. Over the last couple months, we have had sex several times a week.  He is the only one I will do this with. I know some people would be against this, but I want to be who I am and continue to dress this way all the time.


  • The decision to have sex, regardless of the orientation, is an extremely important one that shouldn’t be taken lightly.
  • You have entered into a serious relationship with a close friend and you are happy about it.  Connecting with someone you care about and feeling comfortable with who you are are really important.  It’s great that you are feeling this way.  Consider what kind of relationship you want going forward and how you can achieve that.
  • Any time a teen, regardless of gender or sexual orientation becomes sexually active, they need to make sure that they are engaging in safe, protected sex.  Remember, sexual contact of any kind does carry certain risks.  Please educate yourself and your friend about the numerous sexually transmitted diseases that exist, how to protect yourselves from them and also how to recognize the signs and symptoms of these diseases.
  • Letting your other friends or family know that you are in a relationship can be a difficult choice.  Consider whether you want to tell them and how.  Also think about the pros and cons of not making your relationship public.  Consider how you would feel if the people close to you found out from someone else that you were dating someone.


  • What kind of a relationship do you want to have? What are your relationship goals?
  • What are some of the risks involved in being sexually active and what can you do to protect yourself?
  • If you decided to tell your friends and family about your relationship, what do you think they would say?