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I'm going to assume you've had sex with men, and that if you're reading this you are contemplating your first sexual experience with a woman. Just as the "first time" is all bound up in the cultural myths we hold about sexuality, your first time with a woman will also be significant and, hopefully, wonderful. Maybe your sexual experiences with men have been completely positive. Maybe you've had relationship or sexual difficulties. Maybe you have difficulty reaching orgasm through intercourse and wonder how different things might be with a woman. No matter what your experiences have been you will find many similarities and differences. The first thing to consider is what your expectations are. Your first lesbian experience may not be like it is in your fantasies. Oh and by the way, have you fantasized about sex with women in general or maybe this one woman in particular? Because fantasizing is a great way to let your mind explore places your body haven't yet and may in fact help you get through this first encounter with less anxiety and more creativity. I am not just talking about mental fantasy–masturbation should be part of it. Being with a woman will mean you are with someone who has first-hand knowledge of the female body and if you already know what kind of touching excites you, you will be able to communicate that better. Experiment with different rhythms and types of physical contact and you may be on your way to opening a whole new world of sexual experience. If it feels good for you, chances are it will feel good for her. But don't worry if you don't orgasm the first time or if she doesn't. It's about getting to know what kinds of pleasure are possible. If you both have a good time regardless of how many climaxes you have, you can just look forward to getting better at it next time.
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Communication is key. Many of us think sexual pleasure should be automatic and if we have to ask for what we want, we must not be "doing it right." But asking our lover to do something to give us pleasure can be very exciting! Start out by murmuring or moaning when you like what she is doing, and she will do the same; then you can work up to specifics like "That feels good" or "Don't stop" or "Slower" or "I'm coming!"
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