iragray:

Are you afraid that your dysphoria will render you incapable of having enjoyable sex? Do you avoid having sex (assuming you want to to begin with) because you’re not sure how you’ll react? These are perfectly valid concerns, and no one should tell you otherwise. This post isn’t meant to pressure you into having sex and should not be used by partners of trans* folks as such. This is for those who want to have sex but are nervous about it.

  • Change the way you think about sex. Western culture portrays sex as a race to the finish line. The finish line being the orgasm, of course. Sex is cultural. Therefore, the people who have sex can define sex. So, how do you define it? Do you have sex with your clothes on? Cool. Do you think it’s not necessary to touch your genitals in sex? Cool. You define sex. It’s not some immutable construct that if you can’t conform to then you’re.. not fucked? Change it to suit your needs. You don’t need to change your needs to suit it. Sex is an opportunity to explore someone’s body and to allow someone to explore yours. You can limit what and how you share, and so can they.
  • Talk about your boundaries. Trans* experience or not, this is a conversation everyone should have before having sex with someone. It’s important to know what someone is down or not down to take part in. During this conversation, talk about your likes and dislikes and how you communicate pleasure and discomfort. Some folks don’t feel comfortable talking about sex (or have different abilities changing the way you two or three or four, etc. will communicate), especially when it comes to ourselves having sex, but there are ways around that. Set up number systems, talk online instead, write out your thoughts and concerns in notes, etc. Remember that not all consent is verbal. However you get it done, get to know your partner. During this time, you’ll be able to get a feel for how willing and able they are to respect you and your needs. Do they flub on preferred pronouns and terminology? If so, you may not want to make the beast with two backs with this person.
  • Make yourself comfortable. Emotional concerns are sometimes out of our control, so this is not what I mean. I mean, make yourself physically comfortable to the best of your ability. For example, while I need to bind, I’m incredibly uncomfortable when doing so. The last thing I want in bed is to worry about adjusting my binder, to worry about it rolling up, or to worry about my chest coming out the top. I wear a sports bra during sex usually, and I generally keep a shirt on. What I wear and how much I wear depends on how comfortable I am in the situation with myself, the other person involved, and where I’ll be before, during, and after. 
  • Explore. I’m not saying toss your boundaries to the side. If you want to have penetrative sex because that’s what makes you feel the best, find a way to make it happen. Shut off the lights. Put on two pairs of boxer briefs and stick a brush in between with the handle coming out the front if you don’t have the money for a hard packer. Use your fingers while in positions that make you feel the best. Take part in mutual masturbation in positions that make you feel good about yourself, your body, and your identity. 
  • Learn from past experiences. Sometimes, bad experiences are too triggering for us to want to keep at something, sex or otherwise. This is understandable. If, however, you are able, keep a sex journal and/or communicate with your partner about how things went. For me, I like to talk about sex before having it, while having, after having it, and a couple of days after. Oftentimes, how people feel about what happened changes with time. Consider how things made you feel. Sometimes it’s not a particular position that makes you feel icky but rather the clothes you’re wearing or not wearing or perhaps the day you had before having sex. The list goes on. Be mindful of how your surroundings and your emotions affect how you experience sex. Keep in mind that we don’t always want the same kind of sex all of the time. Make notes of your observations and communicate said observations to your partner or future partners in order to facilitate better sex. 

Conversations and factors that are incredibly important to consider. Still working on that whole “brave enough to communicate what I want” thing, but posts like this help.