A: We actually don’t recommend the use of numbing creams, because they mask the pain that tells you when it’s time to slow down or back off; not being able to feel this pain can lead to injuries like anal tearing.

There are other measures you can take to make anal sex less painful and more enjoyable. Lubricant reduces friction and makes anal penetration easier, so try adding some lube if you’re not already using it–and if you are already using it, try adding some more. Again, don’t use anything that contains any sort of numbing agent, and if you’re using latex condoms for protection, don’t use anything oil-based, because that will break down the latex; there are many water- and silicone-based lubes on the market, and you can experiment a little to find one you like. You also want to be patient and try to take it slow. This can mean simply waiting until you’re turned on and feeling good (perhaps even having an orgasm first), or starting with something small like a finger or anal toy before moving on to anal sex, or both. Finally, it’s important to communicate with your partner, and let him know if you’re feeling discomfort and need him to slow down or stop.

Check out these respected books for more information:
The Ultimate Guide to Anal Sex for Men – Bill Brent
Anal Pleasure and Health – Jack Morin, PhD

So I was wondering if you would have any suggestions as to another “tool” a could use for this. Keep in mind, I am underage and thus have no access to adult toys, and do not want to deal with the added difficulty/risks of buying a legit plug or dildo.

So the thing I want is:
Longer than chapstick
Rounded top (not needed, just an added bonus)
And available in my current situation

A: It is difficult not to recommend specially designed anal toys because they are the safest thing to put in your anus. If you use something without a flared base, you run the risk of getting it stuck up there and requiring a trip to the hospital. With that in mind, perhaps you can try some type of fruit or vegetable that is long enough so that some of it hangs outside of your anus, so you do not run the risk of losing it. You also have the option of shaping the fruit/vegetable however you like. You may also be able to get away with using some hair and body product containers like conditioner or lotion bottles.

If you can browse the net in privacy check out jackinworld.com (not a porn site) as they may have tips for anal masturbation for men.

A: Here are a few tips for making anal sex enjoyable:

1. Let your girlfriend call the shots! The more comfortable she is, they more likely she will enjoy it. Check in frequently with her to see how she is feeling. Many people give up on anal sex because their partner wasn’t sensitive.

2. Use plenty of lubrication. Water-based lube is readily available at most drug stores, and is compatible with latex condoms. Because the rectum is designed to absorb water at the last stage of digestion, you will almost certainly have to reapply frequently. Also available and compatible with latex condoms is silicone-based lube, which lasts a lot longer, and many people do prefer it for anal sex.

3. Consider using a condom. There are many STDs that can be transmitted via anal sex, and it makes clean-up a snap! Speaking of which, many people do prefer to take an enema before receiving anal sex.

4. Start small and size up. You might want to consider lubing her up and slowly inserting one finger, then as she becomes comfortable with that, two fingers, and so on until she is ready for your penis. Going slowly makes the process of opening up the anal muscles more enjoyable, and helps your partner relax into the experience.

5. You may want to try stimulating your partner’s clitoris, vagina, or anything else that she finds arousing before, during, and after anal. The more aroused she is, the better the experience will probably be for her, and the more likely she will be to try it again.

6. Help her relax. Many people find that setting the mood helps a lot: Plenty of room, quiet music, soft lighting, etc. You might want to consider using a dark colored towel or sheets for the occasion so you don’t have to worry about stains. One position a lot of people enjoy for their first time is lying flat on their backs with knees bent – this can help to relax the back, abdomen, and muscles of the pelvic girdle surrounding the anus.

7. When finally inserting your penis, go very slowly. The rectum is a lot more fragile than the vagina, and the sensations are different. The nerves in the rectum mostly register a feeling of fullness, so the initial penetration is likely to be the most intense. Inserting the penis almost in slow-motion can help you both make the most of this initial penetration. Depending on your penis and her colon, you may not be able to insert your penis all the way. If you feel like you’ve hit a wall, you probably have hit the wall of the colon as it bends at the end of the rectum. This length can vary considerably from person to person. Once inserting your penis to the maximum depth that’s comfortable, just stay there for a minute or two, letting her body adjust. Then you can start moving in and out, again in slow motion, until you get a feel for how fast she might most enjoy.

8. Anal sex should not hurt. If there is any pain, discontinue. Again, the rectal lining is very fragile, so there is often a small amount of blood. However, if there is pain or more blood than a little spotting, a quick trip to the emergency room would be a good idea.

You can find more answers to this and many others on our FAQ.

A: Lots of men of all sexual orientations enjoy butt play. All men have a prostate gland that many find intensely pleasurable and is sometimes compared to a woman’s G-spot, or sometimes called a P-spot. To locate the prostate gland just insert your finger (using some lube) into your anus and gently probe about 3-4″ deep along the anal wall towards your stomach. You might even consider getting a dildo for yourself. Here is a website where you can buy a nice selection of anal toys.

Many men find that lying flat on their backs on a towel with their knees bent is a good way to start experimenting with anal play. Don’t forget to use plenty of lube! Water-based lube can dry out quickly, so you might have to reapply frequently. Silicone-based lube lasts a lot longer. Both of these types of lube are compatible with latex condoms. You might even consider using a condom on your toy for easier clean-up.

-The SFSI Staff

A: Yes, going from anal penetration to vaginal penetration without washing in between can cause problems. What you describe is most probably a bacterial infection and easily taken care of with antibiotics. Just go to your doctor or any health clinic and let them know what happened. What happened is quite normal (plenty of folks make this mistake sometime) and not serious unless left untreated.

You can move from the vagina to the anus without problem, but the other way has the potential to cause problems. We all have certain bacteria in our rectum that live just fine in that environment, but when introduced in the vagina they get out of control and cause an infection.

In terms of anal sex, there are a number of things you can do to successfully have painless, erotic, fulfilling and great anal sex. If you would like to know more about that, please feel free to email us back and we can give you some advice and even other resources (books, web sites, etc).

A: You and your wife are already doing most of the things we suggest for good anal play. You probably already know that there’s not really such a thing as too much anal sex, especially the careful way you’re going about it. A small amount of blood (a few smears on toilet paper) after anal sex is something that happens to a fair number of people, even if there is no pain during or after the sex. It’s new in your experience so to narrow things down here are a few suggestions.

• Are you douching with water or the fluid that comes in the commercial douches? We strongly recommend using warm water and not the commercial fluids. You can easily replace the fluid.
• Try using a narrower strap-on and see if that helps.
• Re-visit the basics. Even though you’ve been doing this a long time it might not hurt to review the practice of anal pleasure. We recommend the books The Ultimate Guide to Anal Sex for Men by Bill Brent or Anal Pleasure & Health by Jack Morin Ph. D.

As a person ages all their tissues become more fragile. It’s not “all downhill” after 30 but the early 40s is a time of change in hormones and health for many men. If the above suggestions don’t show improvement for you – i.e. the blood keeps happening – it’s time to go see a medical professional. In fact, if you’ve never had a rectal exam or it’s been a few years we strongly suggest visiting the proctologist or get a referral from a general care physician. You may have concerns about telling a doctor about anal sex. Doctors are professionals with practice hearing all sorts of things but they are also people with personal judgments. If they do not treat you or your condition seriously please don’t be discouraged. Your health and your sexual relationship with your wife are the important outcomes.

If it turns out there’s nothing wrong health-wise you may need to talk with your wife about some changes to the routine. Reactions to the blood could be minimized by knowing that it’s just a part of anal sex. Alternately, you could try receiving anal sex once a week for a month and see if that’s enough for you both or adding other activities you both find sexy.