Q: I'm a gay top -- I don't let anything up my butt, not even fingers. The thing is, I recently found a great guy, and I'm beyond excited to start thinking about a future with him. The problem is that my penis is too big for my partner. Some problem to have, right? I really, really like this guy. What should I do? We sexually please each other in many ways, but do I need to find a guy who can take my penis in order to have long-term sexual happiness?
A: It is some problem to have, and one that I didn't entirely believe was legit until I got confirmation on the source of this question. Now that I know that you are a real person, I'm happy to help you clear this hurdle so you can get to the one-cart grocery shopping, the two-seat tandem biking and all the other things that happy couples do when they're excited about their future together.
Two sphincter muscles surround the anus: one around the opening that's controlled voluntarily, and another further inside the anal canal that's involuntary. The latter is generally the culprit when couples are having a tough time with anal sex. Its job is to help keep the canal closed until you're ready to pass feces. Trying to push past this muscle when it's not relaxed and ready to party will result in a jarringly sharp pain with which many of us are all too familiar. When relaxed, though, this muscle will let just about anything pass.
I doubt you're packing something with a circumference greater than 9 inches -- size of the popular Mr. Universe anal dildo by Tantus -- so your problem should be solved simply by waiting until your partner is fully relaxed before trying anal sex again. Orgasms do an excellent job at that, so get him off first. Since the anal canal doesn't provide adequate moisture on its own, additional lubrication is mandatory, so make sure you're using enough silicone or water-based lube.
Start by inserting one finger gently into your partner's anus, then work your way up to two. Then try a small dildo. Before you deploy your pants soldier, he should be beyond comfortable and begging for more. Be mindful that the anal canal angles toward the front of the body. Putting pressure against its delicate tissue can cause pain, and cause that involuntary muscle to contract. Perhaps most important, don't rush the sex. Opening up the canal takes more coaxing for some than it does for others. Go millimeter by millimeter if you have to.
There are desensitizing gels that numb the area, but I strongly advise against them. Pain has a purpose: It tells you to stop whatever you're doing right now before you cause some serious damage. The last thing you want to do is to tear the skin around or just inside your boy's anal opening. These fissures can be painful and prone to infection, and might scare him off of anal sex for quite a while.
You sound like a seasoned top, but is he an experienced bottom? Sometimes people are embarrassed by their lack of sexual experience and don't reveal it right away. He has to know the basics, so talk with him beforehand about the steps above. He can also experiment with dildos and butt plugs on his own, which will help him to relax with you.
It is essentially impossible that the two of you will never fit together. Relieve him of anxiety by being patient and understanding, and taking the necessary precautions. The excitement of a new relationship can make it hard to abstain, but the early work will pay off and you guys will be just fine.
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