Dear J,
I don't have a lot of gay sex experience and neither does my boyfriend. He has been with one other person and I haven't been with anyone else. We mostly have oral sex but would like to try anal. He wants to top and I don't have an issue with that, but every time I try to bottom it really hurts. I can only handle it for a couple minutes and then I just give up. Can you give me any tips?
Dear Bottomed Out,
First let me start off by saying that I am not doctor so the advice I'm going to give you is only from my own experience. Second, please, please, please practice safe sex. Make sure your boyfriend always wears a condom and you always use safe sex practices.
Anal sex can be very satisfying for both parties. Pleasure can be derived from the nerve endings around the anus and the anus itself. It is an extremely intimate act that should bring you and your boyfriend closer together on so many levels. There are a few things you can try to help ease yourself into it so to speak.
The first thing I want you to do is some "self exploration" on your own aka I want you to explore your own butt before your boyfriend does.
-Find a nice place you can relax. A warm bath is nice or shower.
-Rub your fingers on the outside of your anus. If you're in a bath or shower make the area wet. If you are on "dry land" try some lube.
-Slowly insert a finger. Take a couple breaks, relax, and probe the area again. Each time you go back in things will be more relaxed and it should be easier.
-Next grip and release your sphincter muscles. (it's like clenching your buttocks) This is actually a form of male Kegel exercises. This will help you have control and will also feel good for your partner. The sphincter muscles can also expand and contract on their own when something is in there so it's good to know how this happens.
-Move your finger back and forth. Once you are comfortable with one, try two fingers, then try three. Try masturbating while you're doing this if you like. Remember to stay relaxed.
-Next move one finger around inside until you find your prostate. The prostate gland is a muscular gland encircling the urethra in the male that produces much of the seminal fluid. It is located just under the shaft of your penis. You will know when you find it because the sensation is very unique. This is also a very healthy practice to do. It stimulates blood flow and helps prevent cancer. I suggest you explore your butt every time you get a bath or shower until you are used to it. It's also a good activity to do daily. It will help you stay more relaxed during sex and it's healthy for you.
When you feel ready to try "the real thing" in your butt, have your partner do the above activities to "loosen you up." To avoid pain the key is patience. A lot of guys rush into it and start pounding away that's why it's painful! Before you actually have the penis inserted there should be a lot of fingering, tongue play, and perhaps toys. (Dildo, butt plug etc.) Be sure to use lots of lube. (There's special lube for anal sex that will help numb the area as well.) Anal fingering is an effective way of stimulating the prostate gland and can bring the receiver to orgasm without the penis being inserted. Make this a fun activity before you try his penis.
When it's time to insert the penis make sure he is a wearing a condom and use lots of water-based/condom friendly lube. Your partner should rub his penis all around the outside of your anus. Occasionally adding some pressure but not completely entering. It's like "cock teasing!" This actually drives me wild because of the anticipation. Next, slip the tip of the penis in. This is where the term "Just the tip!" came from. Have him hold there for a bit till you're relaxed, then have him go in further. It is ok to stop a few times, relax and try again. You may need to add more lube. Communication is the key. He should know by your facial expressions if he is hurting you, but speak up anyways.
Your booty can accommodate just about any size penis unless he is hung like an elephant. It is just a matter of relaxing the muscles. Have him go inside you for a bit and then pull out for a break. Each time you do this the sphincter will be more relaxed. You may feel some pain but it should start to subside to pleasure and then he'll be able to stay in longer and start to move back and forth and in and out.
Once you are completely relaxed and get the hang of it, you'll start to experience a lot of pleasure. The constant probing and massaging of the prostate and nerve endings of your anus could make you produce an anal orgasm with or without ejaculating. You could experience multiple anal orgasms and even ejaculate from your penis without your partner even touching it. Your partner may actually feel your orgasm. He should be able to feel the rapid, rhythmic contractions of the anal sphincter, and the prostate while he is inside you. All of these things have happened to me and they are amazing. Don't be discouraged if they don't happen for you right away. It takes patience and relaxation. Good things are cumming! See gay sex is sooooo much better!
Good luck with your probing activities, be safe and remember...
Make good decisions,
J
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