I don't think there's any way of preventing him from feeling that way. Just keep a positive attitude and reassure him that you don't mind and don't mind keep trying. Just say something like how you get to enjoy a little more time with him in bed or whatever.

>>17360763
Give him a blow job, or 69 if you're still trying to get off.

When I 69 my girl, I don't know what it is, but she gets deep as fuck, must be a good angle or something I dont' know, but I dont' get deep throats unless we're 69ing.

first of all, get over the conditioning that penis-in-vagina is the only form of sex. My boyfriend is a trans dude (as in, yeah, he has a vagina) and we have great sex. Think outside the box

>>17360763
Get him the blue pill

As a man with ED, just get a blue pill. Nothing you can do is going to make him feel better and every failed attempt only makes it worse.

moreso than trying to fix it or whatever, my question is what can i say after the innevitable happens?

>>17360827
Kill yourself

>>17360763
wear a strap on a fuck him in the ass

>>17360960
>Kill urself XD
Am I going to have to tell your parents your on 4chan?

>>17360827
was he/she born with a vagina or did he mutilate his penis into a disgusting fake vagina?

>>17360763
do you look like pic related?

If so, I doubt he's going to have a problem.

>moreso than trying to fix it or whatever, my question is what can i say after the innevitable happens?

Probably nothing correctly.

He is likely to react, in a worst case scenario, in one of two ways.

Uncontrollably sad.
Super angry.

Both are because he is going to feel completely worthless. So, don't get angry back if you really like him. And don't start telling him it's okay if he is sad...because he will probably get angry.

He is not angry at you. He is frustrated at himself that a part of his own body doesn't work right.

He feels like a woman would feel if she had no breasts and no vagina. Just a hole to pee out of, because that's what he feels like.

He will be upset because he feels like he can't please you.

Things to do:
Don't get mad, don't give him pity.

Get the blue pill, tell him you love him and want to share sex with him and have him go to the doctor to get them. Tell him you understand it's embarrassing and that you will go with him, looking as beautiful as you can, be on his arm and wait for him in the waiting room so everyone will be jealous he gets to have sex with you. Tell him you are the only one you want to fuck. (say it like that as well, it will work better) Tell him you don't care if he pops a pill as long as you two can enjoy each other.

Get a cock ring. Not a steel one. Get a rubber like stretchy one, this helps hold the blood inside his penis even when it wants to go soft, this will help him get hard again if it starts to go soft. (the rubber version is in the case you need to cut the cock ring off, just be careful doing it) If he starts to go soft, flip him over and start 69ing. This will do two things:
1. Start stimulating him with your mouth to get him erect.
2. Allow him to feel better about himself because he is still pleasuring you.

I've been in your shoes. These worked for me.

But I say again...don't get angry, don't give him pity. Just be there with him and let him vent if he needs to.

>>17361086
wow okay thanks. do you have any actual lines that i can say? cause up til now i was under the impression "its okay" was suitable enough but at this point i think id just say "uhhh" for lack of a better response

if he is able to get hard in the first place there is one viable and super effective answer: a Cockring.

I had a really serious diarrhea and sleppt three days 20+ hours a day and my system was dehydrated and my blood flow was at its all time low so far, but with a cockring I was still able to fuck my GF, when I even would have cummed while I was soft during the day.

It helps and works and involves little risk, if its made from an elastic material and you put it off, when it hurts.

>>17361099
not the guy above, but i would guess the truth:

you are here with him not because of the sex alone but because you like [a lot of things you like about him] and that you are aware of it but will not leave him or be mad at him. of course only if that is the truth.