Gay Anal Sex Ed:

Learning the joy of being fucked in the ass painlessly

By Thomas Kraemer, Jan. 1, 2006

CAUTION: The following page contains serious sex education material and sexually explicit advice for gay men based on the experience and opinions of the author. Readers should beware that the author's advice may not work for everybody and it might even be harmful to some people because everybody is different. Readers are expected to also seek professional help from a gay-friendly doctor or counselor to avoid harm. All referenced web links are provided for free without any compensation of any kind or other conflicts of interest.

Seven basic steps for gay anal sex without any pain:

1.) Clean out your ass (to avoid a mess and skin abrasions)
2.) Turn-on with foreplay (cuddle, kiss, get hard, jerk off, suck, etc.)
3.) Rim job (ass licking)
4.) Lube and finger your ass (to relax the asshole muscle)
5.) Dildo fuck your ass (to stretch it and lube it inside)
6.) Put on a condom (to prevent sexually transmitted infections)
7.) Fuck and cum (without any pain)


I did not learn anything about gay anal sex until my freshman year in college. When I first heard about it, I wondered how anybody could enjoy being fucked in the ass. As an enthusiastic cocksucker, it was easy to ignore anal sex until the first time I watched a porno video of two gay guys fucking. I was surprised that the sight of gay ass fucking made me so horny and interested in losing my anal virginity. I needed no further explanation the first time my cock, without being touched, started shooting cum when a hard dick was shoved up my ass.

My high school sex education classes taught me nothing about gay sex, except that condoms must be used to prevent AIDS. A simple Google search for more information only provided me with many safe sex and porno web pages. Safe sex is important, but since information about it is easily available elsewhere I will avoid repeating most of it here.

However, good instructions on how to ass fuck are much harder to find. For this reason, I describe below how to enjoy being fucked in the ass without any pain. Perhaps reading this will spare you from repeating the mistakes I made. Of course, what works for me may not work for you because everybody is different. But don't give up too soon since most people require lots of practice.

Also, before giving up, check out the list of good web page links and books at the end of this page. The links are current as of Jan. 2006. If they are rotten by the time you read this, you might be able to find equivalent pages with a Google search.

One of the biggest fears of gay virgins is that a dick will be too big to fit in their ass. For example, the following note was posted on the Internet by a 21-year-old senior at Penn State University:

"So my friend and I made it back from the club the other night and started going at it pretty hot and heavy. We got down to nothing pretty quickly, then between the panting and the grunting agreed to fuck each other--except, neither one of us had ever done it before. We whipped out the condoms, put them on, and tried to have a go at it (in the dark). Maybe we're fucking stupid or something (no pun intended) but we couldn't do it. I think we are both too tight, but I'm not sure. Neither one of us could seem to get it into the other. We both wear Lifestyles large condoms, is there a chance we could be *too* big for penetration? I sincerely doubt that, I mean, we're not that big. I asked him and confirmed that neither one of us has ever had so much as a finger up our asses. Does anyone have any advice for first-timers?" (Quoted from

I remember having the above concern when I was an anal virgin. The first time I played with a dildo, I recall thinking that it would never go inside. But with lots of lube, along with slow and steady pressure, the dildo popped through my anal ring just before I was about to give up. Unfortunately, the resulting flash of pain made me to pull it out too quickly, which only caused even more pain. Sure, it fit, but I was still left wondering if a dick could ever fit inside of me without any pain.

I went searching for answers and learned that it is normal for asshole muscles to clamp tight when pushed from the outside. Experienced bottoms (guys who like being fucked in the ass) told me that even the biggest dick will fit provided the asshole muscle has been properly relaxed and slowly stretched open. But nobody could tell me exactly how to do this.

One gay buddy reminded me that my asshole regularly passed shits that were bigger than most dicks. To him, this was proof that a dick would fit in my asshole. Apparently, special nerves allow shit to automatically and painlessly open up the asshole. The trick to painless butt fucking is learning how to relax your asshole muscles just as you do when you take a shit. Unfortunately, few anal virgins are able to do this naturally without any practice.

It is best to practice alone first, without a partner. That way you can relax, go at your own pace and not have to worry about pleasing a partner. Anal play will also toughen the skin around your asshole, which will prevent painful abrasions when you finally get fucked. You can easily practice most of the seven steps described below without a partner.

It took me several years before I was able to relax with a partner and not worry about any pain on entry. Now, I seem to have voluntary control over my asshole muscles, especially when I am horny and begging to be fucked. And even when I experienced pain on initial entry, I still enjoyed being fucked because the pain would go away quickly if my partner held still for a moment or pulled out slowly and slowly reentered after the pain had subsided.

After you are able to fuck yourself with a dildo without any pain, be sure to find a partner that is willing to do the following seven steps at your speed. Many tops (guys who like to fuck ass) often want to fuck ass immediately and they are used to experienced bottoms that are able to take it. Make sure your partner knows in advance that you are inexperienced and will need him to go more slowly. If your partner is versatile (likes fucking and being fucked), try fucking him to learn how it works. Remember, practice makes perfect.


In addition to worrying about a dick being too big for painless fucking, gay bottoms frequently worry about being "clean down there." Not only is it embarrassing to see shit on a top's dick when he pulls out, but shit is very abrasive, which can make fucking very uncomfortable.

Often, the only thing you will need to do before sex is to wash the outside of the asshole to eliminate any foul odors or tastes. This will be sufficient only if your shits have come out cleanly without leaving anything behind. For many guys, this happens naturally when they eat a healthy low-fat, high-fiber diet and avoid liquor and caffeinated drinks, such as Coke and coffee. Of course, everybody is different and so you will need to experiment with different diets to find one that works.

The best way to determine if you are clean is the "finger test." This is done by inserting a lubed finger in your ass while sitting over a toilet. If you feel any small pieces of shit, you can gently pull them out. Doing this will also pre-lube your ass. Of course, be sure to wash your hands and butt before having sex.

However, if your finger feels messy soft shit inside your ass, you can try washing it out with an enema or douche. Unfortunately, enemas can make things messier because water will often get trapped inside and come gushing out unexpectedly during sex. This is why you should always do anal play over a towel that can be easily laundered. It is also a good idea to have a roll of paper towels and baby wipes nearby to clean up any messes that might occur.

According to some doctors, enemas may harm you and so they should be used sparingly, if at all. Disposable enema bottles can be easily purchased in most drug stores. The Fleet brand is commonly available in the U.S.A. They come pre-filled with harsh chemicals that can give you cramps during sex. To avoid any problems, I will pour the chemicals out and refill the bottle with clean water. Be sure to use bottled water if your tap water is unsafe to drink.

Another alternative is to use the small rubber bulb that comes with ear wax removal kits. It will hold a smaller amount of water, which makes it less likely that water will get trapped inside your ass.

After filling the enema bottle or rubber bulb with clean water, lube the tip and gently insert it in your ass. Slowly squeeze the bottle to squirt water inside. Pull the tip out before letting go to prevent water from being sucked back into the bottle. Hold the water inside for awhile before dumping it in the toilet. You may need to do this several times until the water runs clean.

A cleaning technique I use is to stick a lubed finger in and swish the enema water around to remove any shit stuck to the sides. The pieces knocked off will then easily come out when you dump the water. I repeat as needed and wash my hands and butt to finish cleaning up.

Guys who are heavy into anal play, such as fisting, often use shower attachments that can be stuck up the butt to provide a pressure wash. They do a good job of cleaning, but when used incorrectly they can cause bleeding, which might require an embarrassing ambulance ride to the hospital emergency room.


Foreplay will help you turn-on sexually, which will relax your asshole and make it receptive to being fucked. Cuddling, kissing, jerking off, and sucking dick are some of the ways to get sexually excited and ready to be fucked.

The area around the asshole will become puffy and engorged with blood as you become more sexually excited. Experienced ass fuckers can often feel their asshole lips spread open and beg to get fucked. Inadequate foreplay is probably the number one cause of painful anal intercourse.


A rim job is when your partner licks around your asshole and gently fucks it with his tongue. When practicing by yourself, you can simulate rimming by rubbing a spit covered finger around the outside of your asshole. Try jerking off while your finger tip gently spreads the asshole open. Experiment with different methods to see what feels good.

When you are ready to play with a fuck buddy, have him lick around the rim of your asshole. Make sure he uses a lot of spit so that his tongue can slide and press gently into your asshole. Jerk off and feel your asshole muscles relax and spread open. When he starts to tongue fuck your asshole, it will not be long before you are begging him to fuck you.

Licking ass can spread hepatitis and other diseases. Your doctor can give you a shot to avoid hepatitis. Dental dams can be used for safety, but they tend to be impractical.


Even though a good rim job will make you desperate to be fucked, you should slow down and enjoy some fingering first. Fingering is also something you should first practice by yourself without a partner.

A single finger should be lubed and slowly pressed into the asshole. Spit is good enough for tonguing and fingering the outside of the asshole, but spit does not provide enough lube for insertion unless your asshole is very experienced.

The best lubes are tasteless and water soluble for easy clean up. KY Jelly is a common brand of water soluble lube sold in America. Have fun and try out different brands to find one you like.

Oil based lubes are more slippery and last longer than water soluble lubes, but they can damage latex rubber condoms. Many products, such as some versions of Vaseline-brand petroleum jelly, can also contain other chemicals, which will irritate your asshole skin.

Start with the tip of a lubed finger gently spreading the ass lips apart. Use a slow and steady, in and out motion, so that the finger goes in a little bit deeper and deeper each time. Don't rush and go too fast or it will hurt. If it hurts, slowly pull the finger out and let the asshole muscles calm down. Sometimes wiggling the finger will help it slide further into the asshole. At some point, the finger will snap past the asshole ring and pop into the looser rectum. When this happens, stop and hold still to let the asshole muscles get used to the finger.

Try jerking off with a finger up your ass to discover what feels good. Just before you cum, you should be able to feel the prostate gland because it will get really hard. Some guys will cum just from their prostate being stroked without even touching their dick. Experiment with different angles and pressure to find out how your prostate likes to be stroked.

After you are able to take one finger without pain, try slowly working in two and then three fingers and fuck yourself with them. It will probably take multiple practice sessions to achieve three fingers without experiencing any pain. Remember that you can never have too much lube.

When a partner is fingering you, be sure to let him know what feels good or bad. He can only adjust the pressure and angle of his fingers based on your feedback. If he gets you worked up with three fingers, you will be more than ready to try being fucked.

For safety, make sure the fingernails are cut and filed to prevent any cuts. Surgical gloves can also be used.


Even though being fucked by three fingers will probably make you more than ready to be fucked by a dick, using a dildo first can be helpful. Fucking yourself with a dildo is also a good way to practice on your own while jerking off.

A partner can insert a lubed dildo to prepare your ass for fucking. But I like to insert it myself because I can control the angle and pressure to make insertion pain free. Once the dildo is inside and my asshole muscles are relaxed, I will let my partner fuck me with it. It is also fun to let a partner fuck you with a dildo while he sucks your dick.

Playing with dildos is a great way to learn how to be fucked without pain. It will also toughen up the skin around your asshole so that you are less likely to get skin abrasions during fucking. When you have mastered dildos, a real dick will easily slide in without any pain.

Another benefit of using a dildo before fucking is that you will know if you are "clean" inside. Likewise, a condom placed over the dildo makes for easy clean up afterward. Bacteria can grow in the dildo material. For safety, do not share dildos unless you cover them up with a new condom.

The only problem with the dildos sold in most stores is that they are much too big. Make sure you buy a dildo that is less than 5 inches around (that is about one and a half inches across) and less than 7 inches long. The bigger dildos are too hard to use unless you are very experienced.

Small dildos are very hard to find, but they can be purchased online. A group of San Francisco lesbian feminists make and sell some very good small dildos. (As of January, 2006, some of their dildos that are small include: Acute Ambrosia (5 1/4 long, 1 1/4 in diameter) for $36.00 and Leo Black (7 1/4 long, 1 1/2 in diameter) for $50.00 )

Dildos made from silicone rubber, such as the ones mentioned above, are very expensive, but they are easy to clean and well worth the price.

Be careful using improvised homemade dildos. They can break, get lost inside and damage your rectum, which might require a trip to the hospital emergency room.


When you are both ready, have your partner roll on a condom over his hard dick and lube it up well. It is better to have too much lube for fucking than too little. The prior fingering and dildo play you did should have your ass well lubed and ready to be fucked.

Bareback sex without a condom is fun, but it is not worth the risk of death from AIDS. Only partners who have both tested HIV-negative should risk having bareback sex. And both partners must completely trust that their partner will not secretly fool around on the side and acquire HIV after being tested. Besides, bareback sex exposes you to other sexually transmitted infections that can be expensive to treat.


If you and your partner have done all of the previous steps, you will be good and ready to be fucked by a real dick. Don't rush things. You should practice the previous steps over several weeks, both by yourself and with your partner, to get some experience.

Several hours of foreplay, fingering and dildo action may be necessary for a painless fuck. You should be so excited that you cum in less than ten minutes during the actual fucking part.

There are many possible positions for anal sex. The squatting position is a good one for anal beginners because it allows them to control how fast the dick slides in their ass. In this position, the top lies on his back and the bottom squats over his hard dick. The bottom then slowly squats down letting his asshole slide down his partner's dick. When the asshole muscle has relaxed, you can move to other fucking positions.

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Other guys find doggy style (kneeling on all fours) more comfortable. The missionary position (being fucked while reclining back with your legs spread apart and up in the air) is also popular because it is relaxing and allows both partners to see each other.

No matter which position you choose, give your partner access to your asshole by spreading your butt cheeks. Let him gently press the tip of his dick against your asshole. Add lube as needed. Each time he presses against your asshole, it will slowly spread open wider and wider. You will probably feel your asshole muscles resisting his entry. Do not panic because with slow and steady pressure, your asshole will eventually relax and open up.

At some point your partner will press so hard that the tip of his dick will all of a sudden pop inside your asshole. This will probably take away your breath and it might hurt a little bit. Ask your partner to stop and hold still until the pain goes away. If necessary, have him slowly withdraw and wait for any muscle spasms to go away. His dick will go in much easier the next time.

Some guys like to have the dick shoved in all at once and then wait for the pain to subside. This seems risky to me because it can tear the asshole skin and cause bleeding.

I prefer having the dick slowly pushed in and out with it going a little bit deeper on each stroke. It takes several minutes to get the dick completely inside me, but I can avoid any pain with this method. Besides, I find a slow insertion to be very erotic.

After your partner has completely buried his dick in your ass, he should remain motionless for awhile to allow your asshole muscle to relax. When any pain has subsided, he should start slowly fucking in and out. Be sure to experiment and see what feels good. Have him adjust the angle and speed of his thrusting if anything hurts. Before long, you will be begging him to fuck you faster and harder. You will feel no pain, just pleasure.

Also, be sure to jerk off while you are being fucked. The pleasurable sensations of fucking will send you out of this world. When you cum, your asshole muscles will contract around your partner's dick, which may cause him to cum too. Some guys love to pull out, take off the condom and cum all over your ass, chest or face like in a porno video. If you cum inside, be sure to hold the top of the condom as you pull out so that it does not get stuck inside.

With a little bit of practice you will enjoy being fucked in the ass so much that you will not be able to get enough of it. Unless your boyfriend is a total top, the two of you will want to trade off so that you both get your share of being fucked. It is boring to limit yourself to be a top or a bottom only. Being able to both fuck and be fucked in the ass is truly one of the unique joys of gay sex.


A book by Jack Morin, PhD, "Anal Pleasure & Health," was first published in 1981, with a second edition in 1986, and third edition in 1998. This was the first book to do a good job of addressing anal sex.

A speech by Jack Morin, PhD, "Ten Rules of Anal Sex," can be read at

A book by Bill Brent, "The Ultimate Guide to Anal Sex for Men," is also good.

"The Joy of Gay Sex" book covers more than just anal sex and it was fully revised and expanded in a 2003 3rd edition by Dr. Charles Silverstein and Felice Pecano. It includes many sexy illustrations of gay sex. This is the granddaddy of gay advice books. The first edition was published in 1977 and was written by Dr. Charles Silverstein and Edmund White. The 1992 edition was titled "The New Joy of Gay Sex" and was written by Dr. Charles Silverstein and Felice Picano with a preface by Edmund White. Used copies of the previous editions are sometimes hard to find on the used market, but they are interesting to read to see what has changed over time. Check out the "First Time" section on pp. 91-95, "Anus" p. 1, "Bottom" p. 22, "Bottoms Up" p. 24, "Lubricants" p. 154, "Rear Entry" p. 208, "Relaxation" p. 211, "Rimming and Felching" p. 212, "Safe Sex" p. 218, "Sex Toys" p. 235, "Side by Side" p. 256, "Sit on My Face" p. 256, "Sitting on It" p. 260, "Top" p. 282, "Versatility" p. 301, and other sections.

A book by Dan Savage, "Savage Love: Straight Answers from America's Most Popular Sex Columnist," includes gay sex advice. Savage is the very funny sex advice columnist for the Seattle alternative weekly newspaper

Also, checkout Tristan Taormino's anal advisor (for all sexual persuasions) at

Finally, a British AIDS organization publishes the wonderful "F:S Magazine" to educate young gay men about sex. The Adobe Acrobat PDF versions are worth downloading from (FS Magazine was originally called "Fuck Sheet")


A book by the gay Dr. Stephen E. Goldstone, M.D., "The Ins and Outs of Gay Sex," provides excellent medical advice.

Dr. Stephen E. Goldstone, M.D. also runs the web site that included the following web pages as of Jan. 2006 (be sure to check for any page updates): Anus, Anal sex, Rimming, Oral Sex, Condom Use.

Sample news posting: STUDY: 14% of MSM Intentionally Have Unprotected Anal Sex Friday, April 5th 2002

Sample forum posting: "RE: Can't orgasm from anal sex! (18 April 2001 GayHealth: Ask the Doctors) by: anonymous 05/13/2001 @ 12:53AM Dr. Goldstone's answer to the 18 April 2001 question "Can't orgasm from anal sex" asked for advice on how to ejaculate without masturbating while being fucked. I can vouch from first hand experience that "no-handed cumming" is not just a favorite fantasy of gay porno writers.