So recently I bought myself a prosthetic to enable me to top during sex. In other ways I am a lot more experienced, but I have never topped a guy before. My boyfriend (we are newly together so still figuring a lot of things out) is a bottom and he really wants me to top him. I’m nervous to, honestly. I want him to have an enjoyable time and I fear my lack of experience may take away from it. Do you have any advice for doing this for the first time? I am trans too, though I don’t think that makes much of a difference for this.
Hi there! Lots of warming up is the first rule! How have men previously topped you and what did you like about? You can try “rimming” him if he’s into it. Just ask him how he likes it and communicate with him during sex. It’s fine to ask “Do you like this” “How’s that?” “Does it make you feel good?” Have fun!!
Lube is his best friend. It also might take a little time to get the toy adjusted so it is comfortable for you. Kind of just count on the first few times to be a little awkward and just have fun. Also communication is super important.
By the sound of your message, it seems like you're asking for advice more on how to be a top than how to help your boyfriend be a bottom since I get the indication that he's someone who has done some bottoming in the past. Personally, I'm more of a bottom than a top although I've gone both. The best advice I can give is to try to emulate some of the tops you've been with in the past. What things did they do that you enjoyed? The one difficulty about using a dildo to top someone is that you won't be able to feel when he tightens up or clenches. In my experience, it can sometimes be difficult to distinguish a pain moan from a pleasure moan, and when a bottom feels a pang of pain he tends to clench up, but if you're using a lubed-up dildo you probably won't notice if this happens. So keep that in mind. I would recommend missionary. If he's facing away from you, you won't be able to see his face to get a read on whether what you're doing is good for him or you need to slow down or take a break. With missionary, you can sort of keep an eye on him and monitor how he's reacting while also enjoying the intimacy of face-to-face sex. I also recommend having a discussion with him about this. Make sure he knows that you've not done much topping before, so while you want to give this to him, you need feedback so you know you're doing it right and not hurting him. If you make some type of move during the session that hurts him, you need to know immediately so you can make sure not to do it again. And on the flip side, if there's something that you do that he really likes, he needs to tell you so you can make add it to your topping repertoire. Finally, be conscientious about the dildo you buy. I don't pretend to speak for all gay men, but I'd wager that most aren't able to handle beastly 10-inchers with the girth of a beer can, at least not right away. Pick something that's, more or less, roughly average in size. One advantage that you have as a trans man is that you're not stuck with a penis that's just a single size. As you get more confident as a top and as you and your boyfriend "sync," you can upgrade your dildo to something bigger if that's something your boyfriend wants. Obviously, the size of the dildo should be more a matter of his preference than yours, so if you haven't purchased it already, you might even consider picking one out together. If I think of anything else, I'll let you know. Good luck!
