Talking about sex with trans boyfriend?

[JusticeandMercy]

I've been dating a guy for about 8 months now and I still don't know that I'm quite ready for sex but we have been getting more physically intimate with each other and I do know I'd like to go that far eventually. The thing is, he's transgender and I don't want to trigger his gender dysphoria.
I know each trans person is different, but does anyone have any pointers for how to approach the subject without making him uncomfortable?

(I wasn't sure if this belonged here or on the Gender/Sexuality forum.)

[ska8er]

I don't have much experience with something
like this knowing someone or reading up on it
but all I can say is b open with one another.
Since u have said that u have been physically
intimate I'm sure the feelings have come up so
I would say talk it out its not like u have just met
for the first time. C if feelings r mutual on going
any further.

[JusticeandMercy]

I don't have much experience with something
like this knowing someone or reading up on it
but all I can say is b open with one another.
Since u have said that u have been physically
intimate I'm sure the feelings have come up so
I would say talk it out its not like u have just met
for the first time. C if feelings r mutual on going
any further.

Okay. Seems like a good start.

[GoodBoyPesareKhob]

I've been dating a guy for about 8 months now and I still don't know that I'm quite ready for sex but we have been getting more physically intimate with each other and I do know I'd like to go that far eventually. The thing is, he's transgender and I don't want to trigger his gender dysphoria.
I know each trans person is different, but does anyone have any pointers for how to approach the subject without making him uncomfortable?

(I wasn't sure if this belonged here or on the Gender/Sexuality forum.)
Hi, Can you describe more how he is trans? his body style? sexual organs? feelings? which is male? which is female?

[JusticeandMercy]

Hi, Can you describe more how he is trans? his body style? sexual organs? feelings? which is male? which is female?

He's a pre-op trans guy, meaning he still has "female" anatomy. (I wouldn't use that word when talking to him but I'm just saying it to make it clear for you.) He's definitely shown a sexual interest in me but I don't know that he necessarily wants to have sex yet. I do know, however, that he deals with gender dysphoria (feeling like your body doesn't align with your gender) and I don't want to make that worse while talking about or having sex with him.
Ultimately, it's a question I'm going to have to ask him specifically, but I wanted to know if anyone had any tips for keeping him comfortable.

[GoodBoyPesareKhob]

He's a pre-op trans guy, meaning he still has "female" anatomy. (I wouldn't use that word when talking to him but I'm just saying it to make it clear for you.) He's definitely shown a sexual interest in me but I don't know that he necessarily wants to have sex yet. I do know, however, that he deals with gender dysphoria (feeling like your body doesn't align with your gender) and I don't want to make that worse while talking about or having sex with him.
Ultimately, it's a question I'm going to have to ask him specifically, but I wanted to know if anyone had any tips for keeping him comfortable.
Ok. Here we want help you to have best sex with him. I hope best sex for you with him. I have some special tips for you. But maybe I can't tell them all here. As I know, your sex is female and your sexuality is Bi. But here I have some notes and questions from you. I hope these help you. First please say me how old are you and how old is he?
1. You said "I still don't know that I'm quite ready for sex", why you think this?
2. You said "we have been getting more physically intimate with each other". What does this means? I mean what did you do together until now?
3. You said "He's definitely shown a sexual interest in me". What things he does with you in this way?
4. You said "I don't know that he necessarily wants to have sex yet". It depends that he had sexual relation with girls before this and how?
5. You said "I don't want to make that worse while talking about or having sex with him". You are trying to "keeping him comfortable". I want ask what do you expect in sex with him? What and how do you define your sexual roll and his sexual roll in doing sex together? I mean you must give him a male roll in doing sex.

[JusticeandMercy]

Ok. Here we want help you to have best sex with him. I hope best sex for you with him. I have some special tips for you. But maybe I can't tell them all here. As I know, your sex is female and your sexuality is Bi. But here I have some notes and questions from you. I hope these help you. First please say me how old are you and how old is he?
1. You said "I still don't know that I'm quite ready for sex", why you think this?
2. You said "we have been getting more physically intimate with each other". What does this means? I mean what did you do together until now?
3. You said "He's definitely shown a sexual interest in me". What things he does with you in this way?
4. You said "I don't know that he necessarily wants to have sex yet". It depends that he had sexual relation with girls before this and how?
5. You said "I don't want to make that worse while talking about or having sex with him". You are trying to "keeping him comfortable". I want ask what do you expect in sex with him? What and how do you define your sexual roll and his sexual roll in doing sex together? I mean you must give him a male roll in doing sex.

I'm 18 and he's 17. The reason I'm still a bit on the fence about sex is just that I haven't had much experience with this stuff yet. We haven't gone further than neck kissing/moderate touching (back and thighs mostly) and a little bit of neck/ear biting. I don't think I need to get too far into detail about everything we've done but that's a solid overview. I say he's shown a sexual interest in me based on how he acts in those scenarios and some of the conversations we've had about it. (Again, I'd prefer not to get too far into detail.) I don't know how far he's gone with anyone else before, but I do know he's dealt with abusive partners and partners who only wanted him for sex, which is another reason I'm trying to be careful around the topic.
Mostly, when it comes to sex, I just want to be able to do things with each other that we both enjoy and agree to do. I think that's just how sex should work. I'd be open to try whatever. Also, if by a "male role" you mean a "dominant role" I don't think I "have to" give that to him, if he says he wants to try being more submissive.
I don't know if you're planning to lead up to anything, but if you're just going to continue prying information out of me, I'd rather drop the subject.

[ThisGoodBoy]

I'm 18 and he's 17. The reason I'm still a bit on the fence about sex is just that I haven't had much experience with this stuff yet. We haven't gone further than neck kissing/moderate touching (back and thighs mostly) and a little bit of neck/ear biting. I don't think I need to get too far into detail about everything we've done but that's a solid overview. I say he's shown a sexual interest in me based on how he acts in those scenarios and some of the conversations we've had about it. (Again, I'd prefer not to get too far into detail.) I don't know how far he's gone with anyone else before, but I do know he's dealt with abusive partners and partners who only wanted him for sex, which is another reason I'm trying to be careful around the topic.
Mostly, when it comes to sex, I just want to be able to do things with each other that we both enjoy and agree to do. I think that's just how sex should work. I'd be open to try whatever. Also, if by a "male role" you mean a "dominant role" I don't think I "have to" give that to him, if he says he wants to try being more submissive.
I don't know if you're planning to lead up to anything, but if you're just going to continue prying information out of me, I'd rather drop the subject.
Thank you for your trusting and talking open. I hope this all help you.
1. You said you haven't had much experience. what do you mean? you haven't had experience with anyone? or you haven't had experience with some one with female anatomy(real female or trans)?
2. You had neck kissing/moderate touching (back and thighs mostly) and a little bit of neck/ear biting. I think this is very good for start and finally you will do a nice sex and you enjoy both.
3. You had conversations about sex. This is very good to to know each other, knowing each other sexual feelings, and knowing what do you want in sex from each other.
4. He had partners who only wanted him for sex. So you must know that he had male or female sex partners? and he had male role or female role or both in sex, and he liked which role more? These help you define your role and his role in sex, the roles that you enjoy from sex both.
5. This is very good that you want you both enjoy from sex, this means you like give him pleasure too. But you must find how he can enjoy from sex, you must know that he can and wants to enjoy from his female organs? If he hates from his female organs, maybe you can't be near to his female organs.
6. This is good that you think and talk with us that how sex should work with him. I can't say all details here. If you search, you find many ways of a good sex with a trans.
7. This is very good that you are open to try whatever. This means you are ready to do any thing that helps you to have a good sex with him and both enjoy
8. By a "male role" I mean exactly a "male role". He must feel he is real boy, and you must help him with your feelings and some tools. You must do sex with him, such as you are doing sex with a real boy with real male anatomy and real male organs. sorry I can't write details.
9. If you can't give him a "dominant role" in sex, you are giving him a female role. If you expect your sex be such as two lesbian girls, you are doing wrong. His anatomy is female, but as you said his feeling is male. I think you must talk more with him about his sexual role, and define good roles for you and him in sex.
10. Another thing, you are 18 and he's 17. He is smaller and maybe shorter than you. I know that it is possible that a girl do sex with a boy smaller than her. But he has female anatomy. He must doesn't feel that your body is stronger than him. You must be carefull that how define your sex roles and how sex should work.
11. I am not trying to prying information out of you. You are my friend and I just like help you to sex works with him and you both enjoy.