[leoto]

Hey, hopefully someone can help me with this, and sorry for the long question.

Me and my boyfriend have ben dating now almost 3 months, (I'm 22 and he's 19) and everything's been going amazing, and I think I've found the guy I want to be with for the rest of my life, and he feels the same way.
My dilemma is, when it comes to sex, it's only me that takes it, and he's very reluctant for me to do it to him,

The situation started like this, we had ran out of condoms a while ago, and he asked if I still wanted to do it, we had done it without condoms before, but never like fully completed it lol if you know what I mean haha, but he wanted to do that, and I wasn't really sure as I didn't know what to expect from it and whatnot, but yeah, I'm the one who usually takes it, and there's been a couple time where I've tried on him, but lets just say, at the moment, he's still a bit too tight.

So, a couple a weeks ago, just before we were about to do it again, I asked when I was going to get a chance to actually do it to him, and he said he didn't know, and that honestly he didn't really want me to, so that was a blow to me, so I kind of got a bit upset, and said to him oh well, I guess then I'll never know what sex is like(cuz I've never actually done it to anyone before, he's my first), and then when I said to him "the only thing that hurts me right now, is the fact that I'd do anything for him" and I would, I even said then that if it meant me getting to do that(without the condom), then he could finish inside next time lol, so then he got really upset because he knew I was upset and me saying that really hurt him because he knew I was hurt. To which he said a little afterwards that no he'd do it, it wasn't fair for him to say no to me and that if it's for me, it'd be only for me that he'd do it, then I felt bad because I felt like I was presuring him to do it, but he said no, it was only fair.

Just before we were going to a couple days ago, I said to him if I didn't mind asking him 1 question, and I asked when is it that I'm going to be able to try, then he said I don't know, and that he had to shave first, but then I said to him that doesn't matter to me, but he said it did to him, but then I said or is that your way of getting out of doing it for a while, and he said maybe, so then he starting feeling bad again, and turned away, then I cudled him and told him not to feel bad, and then I had said, the only thing that's in the back of my mind is that it's probably never going to happen, he said it was on the back of his mind too.

Because, I would really do anything for him, and I have, and it's just this one thing, and he can't do it, and it hurts, like it sounds stupid that I'm upset over something like that, but it hurts they fact that he wouldn't be inclined to do something for me. Like I know he's liked me fingering him before and whatnot, but now I don't know how to approach it.

So with all that being said, I think he'll eventually let me do it to him, just not yet, so how do you think I should slowly get him into it, like should I ask to finger him and see where that goes, or ask him to do it to himself so I know how he'd like it?

I know it may sound bad, but I don't even feel like letting him do it to me, seeing as I can't to him, and to make the situation worse, he just got braces on, so now to add to the list of not being able to do something right yet, first being not doing it to him yet, and now he can't really give me a bj as the braces hurt his mouth just waiting for it to get used to it. So with that said, do you think he should be more inclined to let me have sex with him.

Thanks for any thoughts and sorry for the long message, just didn't want to leave anything out.

[smoothy]

Now... keep in mind this is coming from a straight person... but this is my undstanding from my perspective... it might not be 100% accurate but it is as I understand it.


There are tops... and there are bottoms... it varies everywhere between total tops to total bottoms... Total tops pitch but never catch and total bottoms catch but never pitch. The absolute middle is a versitle. They do both or either depending on the situation.

He appears to lean more to the total top side... while you are a versitle at heart.

How do you get him to do it? That's anyone's guess... I would assume it would matter where his heart is really at. Unless he's a total top at heart... he might be persuaded depending on what his real reason for resistance is.

YOU being on the reciving end... bareback... puts yourself at tremendous risk. Unless you know 500% that he is absolutely faitfull, and that he has tested clean for HIV the last 5+ years. Not knowing that you put your health at grave risk by not only performing anal bareback... but increasing that by letting him finish there.

You really need to be able to talk to him and getting his real reasons... until you can... all anyone can do is guess.

[Cat1864]

I think the two of you need to slow down. You have only been together for three months and you are already saying things to hurt each other because you aren't communicating. That doesn't sound like love as much as lust. IF he is never comfortable with the idea of receiving, can you live with that or is that where your 'undying love' draws the line?

Why would he be comfortable with 'receiving' if you make it seem like he is obligated to because "I did it for you"? No one likes feeling pressured into doing something. It puts up a mental barrier to being comfortable with the act.

You talk about trying to take him and him being too tight. So he has tried.

Have you tried talking about toys, lubes, different condoms (you might not be able to get pregnant, but there are other dangers), erotica, etc. Have the two of you looked up information on how to make anal more pleasurable and safe?

[Synnen]

Let me get this straight: You've been dating ALMOST 3 months, and you're willing to take the chance that he will give you a deadly disease just so you can stick your d!ck in his a$$?

That sounds like lust, not love, and it sounds like you're just wanting to screw him, at any price.

I wouldn't let you in MY butt either. You're scary with the risks you're willing to take! Oh wait, let me guess. You've NEVER offered to let someone go bareback less than 90 days into a relationship before. It's only because you LOVE this guy that you're willing to consider it.

PFFT.

If you're truly in love, then you're perfectly willing to NOT have sex for several months while you guys slow down and figure this out, right? If not, you just want to screw this guy and don't really care how he feels about it. He has told you how he feels about it, by the way: He doesn't want your penis in his anus.

So... does he know you're asking for advice here? Is he on board with you in figuring out how to make it happen? I betcha the answer to both is "no".

Slow down. Take your time. It's not about sex unless you make it about sex at this point in your relationship.

[simoneaugie]

Sex in the butt can feel really good if it's done right. I'm a girl, so I don't have a prostate gland but rectal stimulation of that gland can be out of this world, I'm told. Have you gotten pleasure when he does it to you?

Does he realize that he may well be missing out? Sex involves a whole lot more than in and out. It's a far more complicated interpersonal issue than my penis, your penis, my hole, your hole.

At this point you two are just beginners. I hear two boys on the playground arguing about who gets the best spot on the monkey bars.

Yes, slow your roll. He is experiencing discomfort with his new braces? Won't let you enter him rectally? He may not be ready to get fully into the give and take a relationship involves.

Is he your friend? Or is he an adventure, a toy.

Do not run out of condoms!