Straight, bi, or gay—this is the sex & relationships site for all of us.

First timers

You've never had anal intercourse but you crave it quite often. Now what?

Q: I associate anal sex with being gay or contracting diseases; yet, I often fantasize about doing it. So far, I never have. I don't consider myself gay—I have a bisexual girlfriend who is always telling me I should try it. I think I'm ready. What advice can you give a first timer?

A: For most men, whether they know it or not, the anal area is an important erogenous zone because of both the dense concentration of nerve endings around the anal area and the close proximity of the prostate glad to the anal opening. The fact of the matter is, straight, gay, or bisexual, this sensitive area, one which heightens sexual pleasure and intensifies orgasms, might as well be considered the male G-Spot. But how do you get started?

In a poll of 5,000 male BastardLife readers, 43% of you told us that the most pleasurable way to begin stimulating the anus is by lightly touching your partner or having your partner touch you around the anal area while performing oral sex.

James from Portland suggested, "Slowly massage the area with your fingers (be sure to have trimmed nails) and see how your partner reacts. If he seems comfortable, then explore a little and deeper."

Craig from St. Louis told us, "Make sure your fingers are well lubricated. Use ample saliva or lubricants like K-Y [Brand] Jelly. As you move in little by little, slowly, be sure to read his body language every step of the way and you will know how much further to continue going."

Anal intercourse may take quite some time to ease into. In fact, 32% of you told us that your first time was not on your first try.

"It took me more than a few tries," Michael from Chicago said, "so be patient with yourself. But once I was relaxed and ready, making darn sure his penis was highly lubricated, I went for it. He inserted himself into me very slowly, and even then I was only able to handle being penetrated partially, which during my orgasm still felt utterly amazing."

A lot of you, 52%, wondered how to prepare hygenically for anal sex.

Tom from Quebec suggested, "Using a simple over the counter Fleet [Brand] enema is really helpful if you're a bottom because it gives you a confidence that you are tidy and ready for anal sexual activity."

Joseph from Vermot added, "Make sure to clean the anus thoroughly with hot, soapy water before any anal activities. I took a warm bath before. You can even use a finger to massage soapy water slightly inside the rim of the anus. This will also help to relax the outer muscles of the sphincter."

46% of you reported an enjoyable experience once you were comfortable enough to go ahead with anal intercourse.

Steven from St. Cloud said, "On the second time my partner and I were together we went all the way—the more I let him in, both the easier and deeper it was. When I climaxed, it blew my mind."

Paul from New York added, "Just as a slow insertion was important, so to was a gradual withdrawal. If you're a top, pulling out too fast can be very painful for your partner so take it slowly for them."

We all know by now, but it cannot be emphasized enough that protecting yourself by using a condom during anal sex is very important. If one of the partners is infected with a sexually transmitted ailment, the likelihood of contracting it increases much more via anal sex because rectal tissues are more easily torn and viruses penetrate faster than from vaginal tissues.

Key Tip: Take your time, be safe, and have fun.—N.B.

By Neal Boulton at 3:16AM on December 08, 2009
posted by
Wed, 07/29/2009 - 9:10am

I completely concur with these remarks. It is wise to take your time. The cleansing advice is simple and really helpful as well. I don't think I have ever experienced an orgasm like the one I have had through anal stimulation—ever.


posted by
Wed, 07/29/2009 - 9:12am

@manlyman: I agree with you. Slow slow slow, but worth it once you find your way. Very worth it.


posted by
Wed, 07/29/2009 - 9:14am

I have engaged in this with my male partners. I've been the one usually to introduce them to it and and each one has been very very grateful to me. There really is not better orgasm for me than this. It does not make the gay by any means either. I have a rich sexual intercourse life with men, I have merely incorporated this into our regimen. It's amazing really.


posted by
Wed, 07/29/2009 - 9:16am

I love this post. If I am with a man and stimulating him either through oral sex or digitally, I always touch or message him anally. I have never seen a man climax harder than when I am engaged in some form of anal play with him.


posted by
Wed, 07/29/2009 - 9:18am

@fatalfemme I could not agree with you more. Since incorporating this years ago when I am with men, most are blown away by it.


posted by TheLongKissGoodnight
Mon, 09/07/2009 - 1:34pm

I totally agree with all of the comments. I would recommend starting with a little self exploration during masturbation until your comfortable for the launch into orbit. Maybe some devices to help adjust.


posted by Anonymous
Tue, 12/08/2009 - 7:48am

do NOT use "soapy water" to clean inside your rectum. Soap is abrasive and can create micro tears inside of you, which you clearly do not want if interested in safe sex. You can also try a "dry enema" which is getting a plunge syringe and squiring about 10 ml (a small shot glass size) of lube up your rectum. Hold, wait until you have the urge to defecate, and release. It is less "rough" on your rectum then using lots of water and you have the benefit of being lubricated and clean.


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BastardLife Books

A letter from Neal Boulton

Welcome to BastardLife; straight, bi, or gay, we're here for you. Read, look, comment—or subscribe to receive daily updates and exchange messages with our editors. It's easy and it's free. Have a sex & relationship question? Or an experience you want to share? Send it to us, and we'll address it in our You Ask We Advise column. Stay hot, be safe, and enjoy.—N.B.


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