Gay Life/Roles in sexual relationship
Recently, my boyfriend told me he was having concerns about our sex life. We have been together going on one year and have always had a healthy sex life and there is wonderful chemistry between us and a lot of passion too. His issue is that we primarily engage in oral sexual activities versus anal sex. We had had anal sex with each of us being the receptive partner. He has always said that when he is the receiving that it is uncomfortable and he finds it hard to relax, while I do not have that issue. I have never pushed this issue with him because I did not want to make him feel uncomfortable or pressured. He said that he is not sure whether he prefers being a top or a bottom, but he is struggling with the fact that our relationship does not have more defined roles as to who is the top or bottom. We have agreed to talk about this issue and work through it, but are not sure where to start. While I do not have a strong preference for either, in past relationships I have tended to be the receptive partner. I honestly believe that emotionally he would prefer to be the primarily receptive partner and is worried that I will not like or enjoy being the primarily insertive partner, to further complicate things, he is not sure how to relax and enjoy the act as the receptive partner. The truth is I would be fine with that role as long as there where occasional exceptions. So I guess my question is twofold. How do we go about talking about this issue in a manner that is productive and leads to a resolution and how do we work to ensure that he is feeling comfortable and is able to enjoy being the receptive partner?
First of all, it says a lot that you are both willing to discuss the issue and work through it to better your relationship together. This will make the process of working through it much easier - as will the fact that you have passion and chemistry. I do wonder though whether you really need to introduce anal sex as a regular sexual activity into your relationship. You haven't said whether you or your boyfriend particularly enjoy it and I presume from the fact that you engage mainly in oral sex that anal is not a particularly important aspect of your sex life in the first place. I would consider asking him if he genuinely wants it because he enjoys it, or if he is just worried it's a necessary activity in a gay relationship (which it isn't). He may be worried, unnecessarily, that because you don't do it often, this somehow means there's something missing from your sex life. I've known gay men in the past who have engaged in anal sex even though they disliked it because they've felt that it's expected of them because they're gay. You also say you have experience of being the receptive partner in the past - I assume he knows about this because you say he thinks you wouldn't like to be the insertive partner - is it possible he feels that because you've had anal sex in the past, you expect it with him now?
If, on the other hand, you both genuinely want to have anal sex more regularly, it is important you are both comfortable with your roles in order to maintain a healthy sex life. You say you haven't pushed the issue of him finding it uncomfortable being the receptive partner. There's no need to push the issue and make him feel pressured, but you will have to discuss exactly what he finds uncomfortable about being the receptive partner. The only way you can resolve this and go about trying to make it comfortable for him is to find out what he does and does not like about it. There are a lot of factors that go into anal sex going smoothly. The first thing to talk to him about is whether he really wants to be the receptive partner. I know you say you believe he'd prefer it emotionally, but you need to know for sure from him. I would suggest you go about this carefully and make sure you let him know you will not be disappointed with him in any way if he would rather not be the receptive partner after all. Let him know that his enjoyment is important to you because in a healthy relationship part of one partner's enjoyment of sex is the others' mutual enjoyment.
You know your boyfriend so you should be able to work out the best way to approach the issue in regards to his personality and comfort zone. I can only suggest you talk to him honestly, openly and without making him feel as though he has done something wrong (which he probably already knows since you've both decided to work it out together). Be open to suggestion and willing to try something he suggests as long as it's within reason.
The most important things to remember about anal sex, for the receptive partner especially, is how to relax and to use plenty of lube (as a general rule too much is better than not enough). Also, plenty of foreplay that will help relax him beforehand - oral/rimming/etc. Generally, you should take everything slowly and if necessary, reassure him that you'll be careful not to hurt him or go too fast. Because you've been together for close to a year, you should be able to pick up whether or not he's comfortable by his body language, facial expression, etc. Pay careful attention to how he reacts and slow down if he seems uncomfortable. I would also suggest that, to begin with, once you're all the way inside him, you stay that way for a couple of minutes if necessary without moving in and out but with touching/kissing, etc. He is then able to adjust to you in his own time and can tell you when he's ready. You could also try buying a dildo or vibrator and either using it during sex or he could try using it alone. If you were to try this I would buy one that is a similar size to your own penis.
You might also want to ask him if he has worries relating to cleanliness. I know that a lot of receptive partners worry that they will not be clean and this can cause them to be tense, and as a result makes anal sex uncomfortable. If he does have issue with this, he could try douching. They're cheap to buy and simple to use. It's just important to remember that plain, clean water should only ever be used - slightly warm but never too hot and not freezing cold. No soap or other chemicals. You shouldn't douche more than three times in a week and wait around two hours afterward before having sex.
It is also possible to buy lubricant such as AnalEaze that contains a small amount of benzocaine which is a mild anaesthetic. I haven't personally used it, so I can't recommend it and I don't think numbing him is the best idea anyway. If he experiences discomfort or pain, there is a reason for it and it should be dealt with, not numbed. But it's something you could try if you both decided to.
If he is still uncomfortable in the future after you have tried everything, it may be worth trying a reversal of roles - you say you are versatile and have no preference for either role. It may be worth having a trial run, so to speak, at him being top and you being bottom for (e.g.) a week or two and seeing how things work out in that way.
You also should be prepared to accept that he may never enjoy being the receptive partner. Some people simply dislike being on the receiving end of anal sex. Hopefully this is not the case, but you should be prepared for this possibility nevertheless.
I hope I've been able to help in some way and wish you all the best in your relationship.