I’m a 26-year-old male. I’m single and consider myself heterosexual. However, I have been increasingly curious about experimenting sexually with a transsexual partner. I joined the transexual hook-up site TSdates.com and have been communicating with a transsexual that I am very interested in meeting in person. My concern is that during our conversations I have not specifically mentioned that I have never been with a transsexual before. I am concerned that this may create an awkward situation when we first meet. Should I inform her of my inexperience, or should I just remain silent and go with the flow?
Curiosity about broadening your sexual experience is more common than you think. Some people are not brave enough to take the step that you are currently taking. Unfortunately, countless people simply repress their urges or conform to antiquated social norms. For your open-mindedness, we salute you.
Addressing your question specifically, regardless of the context of the relationship or encounter that you are seeking, it is always best to be as honest as you can be with your partner. In your situation, this would mean informing her about your inexperience with transsexuals.
In all likelihood, she may already suspect it. You mentioned that you have spent time chatting online. It is therefore probable that you have already released hints regarding your lack of experience without even realizing it.
It’s quite possible that she is waiting for you to mention it directly or that she is being polite and plans on dealing with that situation when you meet in person. Regardless, the proper thing to do would be to reveal the situation before you meet.
If you are concerned that mentioning your lack of experience could be a deal-breaker that should only reinforce the necessity for revealing it. If your partner is that sensitive about such inexperience, it is best that you find out about it before you meet in person.
In the majority of situations such as yours, being honest will have its rewards. Not only will it reinforce her positive perception of your character, but it will also help in making your first sexual encounter with a transsexual smoother and more enjoyable.