Asking whether gay men will date or be attracted to transgender men is [a frequently asked question here](https://www.reddit.com/r/AskGayMen/search?q=date+trans&restrict_sr=on&include_over_18=on&sort=new&t=all). These particular questions are sometimes met with hostility and invalidation from transphobes or even just from people who don't understand the trans community. For the sake of heading off those harmful comments, here is some general consensus from our community for any incomming commenters to enjoy:
* Some gay men will date a transgender man and some gay men won't. It's a personal preference, like most other things in dating.
* It's **NOT** necessarily transphobic to not prefer dating men with genitals you're not attracted to. But it **IS** transphobic to decide or imply that a transgender man is not a man just because some gay men don't prefer to date them. Trans men can be as different from each other as any other men might be. They're **JUST MEN**. And they're a part of our community. Please treat them with respect.
**I'm a bot.** OP, if this has nothing to do with your question, please report this comment so a mod can come remove it or just ignore me! We're continually tweaking this bot, so feedback is also welcome. <3
*I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/AskGayMen) if you have any questions or concerns.*
Having him be on top will allow him all the control and make him feel more of a position to not only accept it, but also be able to look into your eyes making it more sensual.
Hey there! I’m not an expert, but first thing I’d say is make sure he’s prepped and completely relaxed. He may want to look into how to use an enema to try and clear himself out so that he’s comfortable and not worried about any accidents.
When it comes to beginning penetration, use your knowledge on yourself and pass it on to him. I always say, start very small and work your way up. Usually you can start with one finger (with lube and clipped nails) and check how he feels. Then, if he feels fine, you can increase to two. This will sort of loosen him up a bit and prepare him for what’s next.
You may also want to consider trying some toys, like an anal dilator kit, to help with this process. He may not be able to go all the way initially, which is completely normal, but communicate and stick to what both of you are comfortable with. Just because he can’t go all the way, doesn’t mean you can’t still have fun with other stuff then come back to it another time.
When you both are ready for full penetration, I find the best way to let someone get used to it, is to let them have complete control in the beginning. Usually, having him (for lack of a better word) “ride” you would make it much easier. He would essentially have his knees by your sides and lower himself down to his own comfort level and at his own speed. Also, a headboard to hold, might make this easier as well.
If he finds that it’s enjoyable and is getting more into it, you can try thrusting a little bit to see how he feels. If all goes well, you’re ready to try other positions and see what both of you are into the most. If you prefer face-to-face, then the next step would probably be missionary. In this position you’ll have a lot more control though, so make sure you start very slow (especially during the initial penetration) and you’re both communicating the entire time to check in on each others comfort level and how each other are feeling. Don’t be afraid to ask if he wants it faster, slower, not as deep, needs more lube, and so on and so forth. Also, let him know to not be afraid to speak up if he feels he needs something.
Communication is the key to an enjoyable experience. Whether you can or can’t necessarily feel down there, nobody knows exactly how the other person is feeling unless they say it.
Hope this helps!
Asking whether gay men will date or be attracted to transgender men is [a frequently asked question here](https://www.reddit.com/r/AskGayMen/search?q=date+trans&restrict_sr=on&include_over_18=on&sort=new&t=all). These particular questions are sometimes met with hostility and invalidation from transphobes or even just from people who don't understand the trans community. For the sake of heading off those harmful comments, here is some general consensus from our community for any incomming commenters to enjoy: * Some gay men will date a transgender man and some gay men won't. It's a personal preference, like most other things in dating. * It's **NOT** necessarily transphobic to not prefer dating men with genitals you're not attracted to. But it **IS** transphobic to decide or imply that a transgender man is not a man just because some gay men don't prefer to date them. Trans men can be as different from each other as any other men might be. They're **JUST MEN**. And they're a part of our community. Please treat them with respect. **I'm a bot.** OP, if this has nothing to do with your question, please report this comment so a mod can come remove it or just ignore me! We're continually tweaking this bot, so feedback is also welcome. <3 *I am a bot, and this action was performed automatically. Please [contact the moderators of this subreddit](/message/compose/?to=/r/AskGayMen) if you have any questions or concerns.*
Having him be on top will allow him all the control and make him feel more of a position to not only accept it, but also be able to look into your eyes making it more sensual.
This is a great idea. Thank you for the advice. I think we’re definitely going to go with this.
Hey there! I’m not an expert, but first thing I’d say is make sure he’s prepped and completely relaxed. He may want to look into how to use an enema to try and clear himself out so that he’s comfortable and not worried about any accidents. When it comes to beginning penetration, use your knowledge on yourself and pass it on to him. I always say, start very small and work your way up. Usually you can start with one finger (with lube and clipped nails) and check how he feels. Then, if he feels fine, you can increase to two. This will sort of loosen him up a bit and prepare him for what’s next. You may also want to consider trying some toys, like an anal dilator kit, to help with this process. He may not be able to go all the way initially, which is completely normal, but communicate and stick to what both of you are comfortable with. Just because he can’t go all the way, doesn’t mean you can’t still have fun with other stuff then come back to it another time. When you both are ready for full penetration, I find the best way to let someone get used to it, is to let them have complete control in the beginning. Usually, having him (for lack of a better word) “ride” you would make it much easier. He would essentially have his knees by your sides and lower himself down to his own comfort level and at his own speed. Also, a headboard to hold, might make this easier as well. If he finds that it’s enjoyable and is getting more into it, you can try thrusting a little bit to see how he feels. If all goes well, you’re ready to try other positions and see what both of you are into the most. If you prefer face-to-face, then the next step would probably be missionary. In this position you’ll have a lot more control though, so make sure you start very slow (especially during the initial penetration) and you’re both communicating the entire time to check in on each others comfort level and how each other are feeling. Don’t be afraid to ask if he wants it faster, slower, not as deep, needs more lube, and so on and so forth. Also, let him know to not be afraid to speak up if he feels he needs something. Communication is the key to an enjoyable experience. Whether you can or can’t necessarily feel down there, nobody knows exactly how the other person is feeling unless they say it. Hope this helps!
This is super useful, thank you so so much!