Question: My boyfriend is very big. I started to try anal, but it really hurt. What should I do, City Girl?
Answer: Communication and patience are your friends! This is why I don't recommend having casual anal sex. If you are in a relationship with someone, you should be able to talk about things openly and in advance. There needs to be an understanding that anal sex can't be rushed. Thrusting hard might feel good for him, but if you are in pain, it's doubtful that anal will be part of your sexual repertoire for very long. Think slow and steady.
Pick a night to introduce a finger or two into the mix. Focus on the clit and pussy first, and then ease on into the ass. Have a good lube on hand. Start with a finger or two on the outside of the anus, and then slowly put one finger inside. The goal here shouldn't be for you to orgasm or for the finger to simulate a cock, but rather, to get you more accustomed to anal play.
After you feel comfortable with fingers, try a small anal plug or bead inside your ass. Again, the emphasis is on using the toy to supplement the experience. It helps if you have already cum clitorally or vaginally before you pull out the beads so you will be more relaxed.
When you are ready to have anal sex for the first time, follow the tips that I laid out for you in my Anal 101 post. To reiterate one of those suggestions, I do not recommend having anal sex on a full stomach. That just increases the discomfort and chance that you will feel nauseous or have to go to the bathroom.
After you have reached orgasm with some pussy stimulation and have prepped the ass a bit with a finger or toy, have your man put a handful of lube on his cock and in your ass. Then sit on top of your man with your back facing his chest. That should work no matter his height, weight or "size," and is also the most natural position for your body to relax your anal muscles.
With you on top, you also have more control in terms of how much of his cock you take in and the pace of the thrusts. Remember that both can be gradual and in a manner that is enjoyable (or at least tolerable) to you. If it starts to hurt, take some deep breaths for a minute and then see if it still hurts. If so, stop, ask your man to release his cock, and go to the bathroom.
"Why the bathroom?" you might be wondering.
Well, sitting down will help your muscles relax. There also can be a feeling at the beginning of anal sex that you have gas or have to go to the bathroom. (I'm not trying to gross you out here. This is just the anatomy of things.) Heading to the ‘loo will give you more privacy on the chance that there is any "activity" in that region.
Upon returning to the bedroom, try again. If the act is still painful after a minute or two, then try a different position. What feels comfortable for you will depend on your body and your partner's body. (When I refer to "body," I mean height, weight, how tight your ass is, and how large his cock is.) Be sure to communicate with your partner if you feel any discomfort. Most guys will not be able to tell that you are in pain, unless you speak up! Your partner also needs to know that if you say, "Oww" or "Stop," that he should release his cock from your ass immediately.
As you are becoming comfortable with anal play, know that the sex doesn't have to lead to orgasm – initially or ever. If anal sex is painful or makes you feel like you have to go to the bathroom, don't continue it. Release his cock from your ass, go to the bathroom, grab a washcloth on the way back to the bedroom, wipe his cock down and then enjoy some oral or traditional sex. It's okay to save anal sex for another time. I won't say that the act is like riding a bicycle, but your body and muscles will become more acclimated to it.
There are women who do not enjoy anal sex at first, but after several attempts, find that they not only enjoy it, but also get a lot of pleasure from the act. Likewise, there are those women who don't find the act pleasurable and never want to try it again. Whatever mode works for you and your partner is the right one!