Going soft

[Mystery Man]

omg, lately i have been going soft when i was going to do anal with my bf n its like argghh so annoying, cos we started tryin it n it hurt him so i think i go soft cos i hate hurtin him but we wanna try again so is there like anyway to avoid this from happenin ?

[acholooz]

I'm not speaking from experience here, but perhaps don't rush back in, but do something a bit less for a while like just fingering, one finger first then two, and be sure he's comfortable with that. Try and get him to a state where he really enjoys the anal stimulation of something slightly smaller and is really keen to step back up to the real thing. Then make sure you take it slow, lube up and are really considerate. It seems from the whole tone of your question that you are a considerate guy so that shouldnt be a problem.

One other thought, which both of you would have to be happy with, but how about swapping roles - perhaps you've already done that

[marshlander]

You don't have to do anal to have a lot of fun. I don't think you get drummed out of the gay gang if you try other things for a while.

[Mystery Man]

I'm not speaking from experience here, but perhaps don't rush back in, but do something a bit less for a while like just fingering, one finger first then two, and be sure he's comfortable with that. Try and get him to a state where he really enjoys the anal stimulation of something slightly smaller and is really keen to step back up to the real thing. Then make sure you take it slow, lube up and are really considerate. It seems from the whole tone of your question that you are a considerate guy so that shouldnt be a problem.

One other thought, which both of you would have to be happy with, but how about swapping roles - perhaps you've already done that

yer he started with me first, but then i tried him n it hurt him so i went soft n then he was up for it again another time but i wudnt even stay hard

[princealbertofb]

I think it could be that you are really afraid of hurting him. The advice given here about preparing him well with either fingers or smaller objects sounds like good advice, just to make sure that you are aware that he's ready and won't hurt if you try penetrating him. I think it's the anguish of the possibility of it hurting him that is causing your loss of stiffness. You could also, as suggested, try just masturbating together, or even try a cockring?

[acholooz]

Look it sounds as if you're a considerate and caring couple. Just take it slow, whats the hurry? If you both care for each other it will come right if you give it time.

Don't know how much detail we're allowed to go into, or how personal such questions should get, but his experience could possibly be improved by what we might call the angle of approach. If you were to try with him lowering himself onto you then he would be in control of the situation & what was comfortable.& how fast to go. You've probably tried this but just a thought.

One other thought, if he was up for it again another time it cant have been really that terrible and, I know its easy to say and probably doesn't help, but if he really wants you to do this then you need to focus on that.