Sex help? My boyfriend doesn't sexually enjoy bottoming and it's frustrating!

[Darkkev02]

Hey everyone. I'm a 19 yo guy in a loving relationship with another 19 yo guy. We're both versatile and we both enjoy topping more than bottoming. Sometimes my boyfriend doesn't stay hard while I'm topping him and he says he still enjoys it and that he gets nervous it might hurt or something so he loses the boner. Today he told me the truth and that's when he's bottoming he doesn't feel that good inside his butt...it doesn't hurt or anything but it's not strong (knowing that we have a long foreplay). He says he's turned on and everything and that he loves the connection and the intemacy and that it feels good when i'm stroking him while topping but inside it just doesn't feel that strong. He also sometimes loses his boner because he's stressed and It gets really frustrating for me. I have a fairly average penis and I don't know if he needs a bigger one for his prostate to get more stimulated...Ive suggested the idea of seeing other guys but he said that he only loves me and he would only enjoy it emotionally more than physically with me and thats the most important part to him.
I don't know how to feel about all of this...I honestly love topping and I don't think I can let go of it but if hes not enjoying it as much as I was expecting then maybe I should stop?? He promised it's not my fault and that im a great top but i'm still worried. Help me!!

[VirgoMasquerade]

He's too caught up in his head, Maybe try something relaxing in the bedroom like loads of foreplay and maybe a little something fun that gets his mind off the pain

[Cuddly]

It's normal for the bottom to go soft. Do you stimulate his penis while you top him? That should help.

[LJay]

Is anal sex always the high point of your time at sex? Maybe finding other things to do would give him a break. then the idea would be to look forward to topping and bottoming as a "special" activity. You could also experiment with positions. Anal can be quite a different experience when done with you both on your sides or one riding or with entry from a new direction. You might like to get out of the bedroom for a change, too.

[Camfer]

Try giving him a prostate massage with your finger(s) while jerking him off with your other hand. If that is too much for him, try getting him very close to cumming and then insert your lubed-up middle finger to feel his prostate swell and harden right at the moment of ejaculation. This should be great for him and fun for you too.

Now, compare the length of your middle finger to the length of your cock. You probably will find that your cock is longer than your cock. This means that your cock length is plenty long and plenty big to hit and stimulate his prostate. So now you can let that go.

Next, don't make a problem where there is none. He's willing to bottom for you, and he likes it at least on the level that it's good for you and an intimate connection for the both of you. You should continue to enjoy it and keep the lines of communication open about it. It's great that you are concerned about his pleasure, just as much as he concerned about yours.

[MikeW]

...I don't know how to feel about all of this...I honestly love topping and I don't think I can let go of it but if hes not enjoying it as much as I was expecting then maybe I should stop?? He promised it's not my fault and that im a great top but i'm still worried. Help me!!

Like [MENTION=20933]LJay[/MENTION] and [MENTION=20941]Camfer[/MENTION] said, don't make such a big deal out of this in your own mind. I would venture to say that most of the guys who keep their erections while being penetrated -- the ones you've probably seen in porn -- are taking a virility drug like Viagra or Cialis. It is common for guys to loose their erections when being topped. But it is also highly individual and, as suggested, may be a matter of him learning to enjoy it. Since you're both still very young, I'm going to assume you're both relatively inexperienced. This is not a bad thing, its just that to a degree one has to "learn" to enjoy bottoming. Learn to associate that particular sensation with erotic stimulation. Not all gay men do. Some just don't like that sensation. But it sounds like your BF is fine with it. Sounds like he's enjoying it, or at least enjoying the fact that you're getting off on it, but since he's not hard you can't quite believe or accept it. Frankly I think the "problem" is mostly all in your head. Just stop worrying and have fun!

[meridannight]

he says he still enjoys it

He says he's turned on and everything and that he loves the connection and the intemacy and that it feels good when i'm stroking him while topping

he said that he only loves me and he would only enjoy it emotionally more than physically with me and thats the most important part to him.

above i've brought out the most important information you provided in your post.

f hes not enjoying it as much as I was expecting then maybe I should stop?? He promised it's not my fault and that im a great top but i'm still worried. Help me!!

he's not enjoying it as much as you expected him to? what does that mean? he says he enjoys it, but you're expecting him to do what exactly?

it's not always all about being hard. the fact that he loses his erection doesn't mean being penetrated isn't enjoyable to him (a man can cum while his penis is soft) or that he feels no sexual pleasure from the experience.

you seem to be all focused on one thing -- him not having an erection while you're penetrating him. you need to stop focusing on that one thing. attainment of sexual pleasure is a lot more nuanced than simply fucking and being fucked. at least it can be, under the best of circumstances.

i agree with the others, this problem is in your head.

[Scootaloo]

your young, your both tops, you both have a lot fun times ahead of you.

My advice? Get a bottom bitch that you guys can share. There are plenty of sissy bottom boys who would love to be your sex toy and have no problem staying out of your relationship. I should know I was one of those sissy boys when I was your age.