Ok, I wasn't going to post this on here for getting too personal, but I need to get some advice (don't I always? LOL). So anyway, here it goes.
My boyfriend and I have tried twice now to have anal sex and we haven't been very successful. Now keep in mind we are both very new to this, but the furthest we've gotten has been the head of my penis just inside his hole. He squirmed right after it entered and it popped out and he got frustrated so we went on to other things.
But the problem is, he does get frustrated and upset when it doesn't work. I've done my best to reassure him that it's because we're both inexperienced and both a bit nervous and even a little anxious. I keep telling him that we're just going to have to keep tryin an eventually it will happen.
We are using plenty of lube and all so I don't think it's that. I really think it's a combination of being so anxious to try it and nervous cause we've never done it. But can any of y'all give me some advice? And sorry if I got too personal. 
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Have you tried warming up with a dildo first, some guys have to loosen up before they get the real thing.
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Does he trust you explicitly?
If not, then he may be tensing up and 'scared' its going to hurt thus making things difficult.
Mind not trusting you in this matter is not always a reflection of you, other things can be under all of this causing him anxiety and inability to 'trust' fully.
One thing that may help is cuddling - spooning in the nude, you pressing up against his back, him with his back pressed up against your front. Just laying there, small talking, with your arm around him will relax him and get used to this idea of you being pressed against his back. No intent and no pressure for this to go further. Yes you may be hard and he will feel that, but your all's intent is just to lay there and be intimate.
Side to side 'spooning' position also means you will be able to control your movements a bit and go a lot slower than say doggy style or missionary style (gravity, can't trust it). So when you do get to the point where the idea of insertion seems good, you are not struggling against that terrible gravity and can actually 'poke around' a tad and rest with only a bit of dick in there....
Also try 'teasing' where you use your erect penis to massage his, um, crack.... The intent is not to press forward, but just to get him all hot and bothered with the idea that you are excited and 'knocking' on the back door. It can also be a fun way to lube up, put a bit between his butt cheeks above the anus and rub the shaft of your penis up and down the crack....
You might also want to try with him sitting down on you. This puts him in full command here and gives him the feeling of control thus he may actually relax a lot more into.
Since this is all new, its a tad scary. We all know that its going to hurt - thus we tense up a bit out of fear of the pain. Relaxing and getting use to the closeness (while fanning the flames of passion) drives that fear further down the road and makes more things possible.
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Bowyn has some good tips.
I think we each have our own way of ending anal virginity. Of course you know lots of lube and take it slowly. If I'm introducing a partner to being an anal bottom, I like to get him off either using my hand or my mouth while I insert my fingers into him, one at first and working to two or even three. Then no rest, I slowly take him. He's pretty relaxed and still thinking about just having ejaculated, so he isn't going to tense up much, and he'll relax again each time I stop pressing in. When he relaxes, I press in a bit more. Maybe tops five minutes and he's bucking against me - I've found his prostate by then and, he's learned that, though it hurts a little, it isn't anything to tense up over, and, just going with it makes it feel better.
The biggest thing is the bottom needs to relax, and the top needs to go slow and, neither of you can get frustrated with the time it takes to get it right the first few times. Position isn't that important but, I'd save spoon for later as that's the most difficult one to stay inside your partner doing. Even this old dog ruins that one by popping out too many times now and then LOL.
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Share a six pack... 
 Life's too short to miss an opportunity to show your love and affection!
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Thanks guys! I'll definitely keep all these things in mind next time. Yes I do think that he's a bit "scared" because he has said both times right before to "go easy" and "be gentle" which I do my best to do just that. As far as a dildo goes, we've talked about "toys" and even looked at some online, bu have yet to buy any.
We have tried the "teasing" with my penis while lubing and we both liked that, but like I said originally I think part of the problem is we're rushing the foreplay! That's why I kinda like the "spooning" idea you mentioned Bowyn. :biggrin: I think I'll try that next time.
On a side note, I would like to say that it's not just about the sex with my guy, although it has been AWESOME so far. But just lying in his arms, or he in mine, even just walking through a store with him by my side is so incredible. It may be a little early on in the relationship, but I really think I'm falling hard for this guy.
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Oh and Rox, he's allergic to the hops in beer! So that probably would not be a good idea!
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I'm glad you found each other and, that six pack doesn't have to be beer, it could be mudslides, wine coolers, whatever you both like
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Quote:I keep telling him that we're just going to have to keep tryin an eventually it will happen.
Not a good thing to say to 'take the pressure off' I'm afraid.
The inability to have successful and comfortable anal sex usually comes down to performance anxiety. The spincter muscle is one of the toughest muscles in the body and it needs to be relaxed to 'let it in' and if their is anxiety and fear, then that lil muscle is never going to relax enough.
Of course, some people are just not built for anal penetration and that is something you both have to consider and accept and find alternatives.
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dfiant Wrote:Not a good thing to say to 'take the pressure off' I'm afraid.
The inability to have successful and comfortable anal sex usually comes down to performance anxiety. The spincter muscle is one of the toughest muscles in the body and it needs to be relaxed to 'let it in' and if their is anxiety and fear, then that lil muscle is never going to relax enough.
Of course, some people are just not built for anal penetration and that is something you both have to consider and accept and find alternatives.
So other than the techniques already mentioned, what else would you recommend to alleviate the performance anxiety? Don't get me wrong, everything else we've done together as far as sex goes has been terrific, but this is something we both want to share with each other and I'll be damned if I give up without a fight!:biggrin:
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