How can I stretch it/ hae anal sex without it being unbearable?

Might not be possible.

Is he using a ton of lube. Like imagine how much you think you might need - double it - then double it again?

Are you having clitoral or vaginal orgasms first - if not - it will hurt. The anus does not orgasm - so it doesn't natural enlarge to let a penis in.

Is he first using a finger or a sex toy? First timers especially can rarely can anything bigger than a finger in.

Personally I HAAAATE it because it's so unbareable. I even envoked the "no anal sex" rule with my ex fiance. However this new guy I'm seeing and a guy friend of mine say that if the girl lays on her back and the guy enters her anus as if you were having missionary sex it's a lot less painful. I have yet to try it, (my rule may still be in effect, I haven't decided) but you might want to!

I have to say I disagree with what your boyfriend thinks would be less painful. It doesn't makes sense given the musculature. "Doggie" style is the only position for beginners in my experience.

If you can't relax it won't happen anyway. The reciever MUST have complete control of entry, doggie style either you or him can have a hand in front stroking your clit or using a toy there. XXX-tra lube is absolutely essential, even beginning with a finger. Patience is also key, it may take several sessions to even get a finger in.

umm..I'm a boy, just so you know.

(I'm the guy who made the topic, by the way)

I'm a boy.
and I'm not in it for the pleasure, I want him inside me, then him to cum (as fast as possible, prefferbly), then him give me head, or something to get me off. then go to bed.

We are more friends with benefits, not really "boyfriends", or anything.
And please don't make this a "he is just using you for sex" or anything discussion, because we both are. However, weve known eachother since we were kids, and have both never been with a girl, or another guy. We only do this with eachother, no STD's, or anything. So please, mind your own business for those perticular topics, and only respond to the one at hand!

Thank you!

oh yeah, also:

I don't want him to stick his fingers, or anything penis-shaped, or anything into my anus. Like I said, I'm not doing it for me. I want him in, then awhile of fucking, then out. I don't care if I get cum inside of me. (Wouldn't be the first time). Even though in the 2 times weve tried (and every time in the future!) we ALWAYS use condoms. ALWAYS.

Anyway, what I mean is that when we start fooling around (usually starts as a game of strip-poker, or something similar, a contest to see who gest naked first, then who gives who head, then if we still feel like it, anal, well, we WANT to try it, anyways... So far its been unbearable, even with TONS of lube), I don't want him to have to put things in me to get me ready, you know? That wouldn't be very much fun...

I don't care if it feels GOOD, as long as it doesnt HURT!

and by the way, the reason I never give him anal is because well (this will sound like i am making myself look good but...) he is quite a bit...smaller, then me (his rectum and his penis). So we figure, if it is gonna happen, it'll be him to me, not the other way around. Because my larger penis has NO CHANCE of getting into him. we have tried. Last time, he atleast made it about id say a quarter into me before it got incredibly unbearable and I forced him to get it out.

Sorry, but my answer is basically the same - just skip the vaginal/clitoral orgams. If it doesn't fit - it doesn't fit. Some people are just too small. Try fingering. (Well you just said in another post you don't want to do that.) But if it is sex just for sex sake I have my doubts fingering will be what you want to do - so your only other choice is to be into pain. (which you also said you didn't want.)

Use lube,lube, and more lube or skip it. Sorry.