Going Back to the Backdoor

May 132005
 

Many years ago, I had anal sex with a man I was very much in love with. I am now getting involved in a new relationship. My new lover knows that I have had anal sex before, but he does not know how long it has been. My question is: since I have not had anal sex for a long time, will we have to start from the beginning?

–Going Back to the Backdoor

Besides saying “a long time,” you didn’t specify exactly how long it’s been since you’ve had a cock up your ass. A year? Five years? Ten years? If it’s been more than a few years, then you should start slowly. Begin with lots of foreplay and lube and work your way up to one finger or a slim toy, and don’t go any farther than that. Next time, you can experiment with two fingers. You want to re-introduce the pleasures of buttfucking to your ass in a gradual way.

Don’t think of it as a chore, but instead use it as an opportunity to re-experience the first time you ever had something in your ass. You and your guy can revel in the excitement, the slight resistance, the de-flowering of that tight little hole. Relish each new step when your ass is able to take a little more. The body does have memory, so I suspect that it may take less time to build from fingers to your new lover’s dick, but everyone is different. Listen to your body, honor its boundaries, and take it as slow as you need to.

Backdoor Couple

Apr 172005
 

I have recently started dating a girl who, like me, really enjoys anal intercourse. Obviously we are at the start of the relationship and are having multiple encounters that include much anal play and some anal intercourse. We are both well versed in all of the basics of anal play i.e. lube, cleanliness, order of entry etc. If we engage in anal intercourse three or four times a week, should we be concerned about long-term damage to her ass due to such frequency?

–Backdoor Couple

As long as you’re following the general rules for safe and pleasurable anal play — go slow, relax, use plenty of lube, work your way up to intercourse — then you’re not in any danger of causing harm in the short or long term. The majority of people who develop health issues because of anal sex combine drugs and alcohol with their play or push their bodies too far too fast. Make sure your girlfriend listens to her body, and if her ass feels sore or tired, then give it a brief vacation; otherwise, have as much anal play as you like. In fact, anal sex can increase circulation to the anal area as well as tone and exercise the anal sphincter muscles. So, the more good butt sex you have, the healthier your butt can be!

Anal Novice

Apr 082005
 

Is there a rule of thumb about eating before anal sex so as not to disrupt anal activity with bowel movement? Should you time meals in a particular way? Should you fast before anal sex, and, if so, for how long?

–Anal Novice

Everyone’s digestive system is different, so there is no universal rule of thumb when it comes to how your gastrointestinal system works. You know your ass, your bathroom schedule, and your regularity better than anyone else. However, as a general guideline, you should have a bowel movement before anal penetration in order to empty your bowels and ‘clear the runway’ for anal play. Eating a big meal before a hot anal sex date is probably not the best idea since it’s likely to stimulate digestion. In addition, if you have a particularly sensitive system, then avoid foods that are spicy or especially hard for your body to digest. I don’t recommend that people fast before anal sex, since fasting can cause a drop in blood sugar levels, and it’s never ideal to have sex while lightheaded and hungry. Fasting can also disrupt your body’s natural processes, throwing everything out of whack.

Pumped Up

Mar 302005
 

My boyfriend and I recently discovered the pleasure of penis pumping, and I’m thinking of getting a vaginal pump. But lately I have been using my guy’s penis pump on my asshole, and I love the sensation and the feeling. I was wondering if you have ever done this, and if it is a safe practice?

–Pumped Up

Many men and women have discovered the joys of pumping. For readers who may not know about it, a penis pump works like this: your cock goes inside a hard plastic cylinder which either has a built-in pump or an external one. As you pump, air is sucked out of the cylinder, and the vacuum-like suction sends blood rushing to the cock. This helps the cock become erect, enhances an erection by giving it a bigger appearance (temporarily), and creates a sucking sensation which many men love. Women can use the same pumping mechanism with the nipple attachment (a much smaller cylinder), which works great on the clitoris. There are also pussy pumps on the market made especially for women. The same principles apply: blood rushes to the clit, making is more swollen (and often more sensitive) than usual. I’ve pumped my own clit, and find that not only is it hot to see my clit all fat and thick, but clitoral stimulation is a lot more intense after I’ve pumped.

I’ve never used a pump on my butthole. The puckered skin of the asshole is sensitive tissue that’s incredibly rich in nerve endings and gets engorged when you’re aroused much like the rest of our genitals. So, it makes sense that when you apply suction to it, blood rushes to the area and creates a pleasurable sensation. Similar cautions for all pumping apply: use a little lube inside the cylinder for a comfortable, easier fit; be careful not to pinch the delicate skin when inserting it into the cylinder; do not over-pump or leave the cylinder on for too long.

Drunken Asswoman

Mar 102005
 

My husband and I routinely do anal play together, and he is tempted to try pouring alcohol into my ass, like wine or vodka. Is it possible to get drunk by ingesting alcohol through one’s ass? Are there any implications from putting alcohol in one’s ass?

–Drunken Asswoman

Not only is it possible to get drunk by having any kind of alcoholic beverage poured into your ass, it’s inevitable. When you drink a glass of wine or vodka, it has the benefit of passing through your stomach and liver, where it’s broken down by enzymes before entering the bloodstream. However, because of the absorptive capacity of the rectum and colon, when you absorb alcohol through your ass, it goes directly into your bloodstream. This means that a much smaller amount will make you very drunk. It’s very dangerous to ingest alcohol the way you describe (essentially via an alcohol enema) and could even result in alcohol poisoning. If you want to drink, do it with your mouth. If you want an enema, use plain warm water.

Woodstock Girl

Feb 272005
 

I love anal sex — much more than vaginal. I love the pressure just before the head pops in and that little ache as it does. What I am having problems with is that everything that goes in my ass seems too long. It feels almost like the dick or the toy is hitting something inside of me, and it hurts. I have a friend I play with and we do a lot of BDSM scenes, especially rape scenes and punishment-type scenes. He would like to see just how much my butt can take, and I do love the width of everything, especially the next day. Can you help me with the length problem?

–Woodstock Girl

Unlike the vagina, the rectum is not a straight tube. It has a gentle curve, first tipping forward toward the front of the body, then away, then forward again. Everyone’s curves are different, and some are more pronounced than others. As a result, if you stick anything straight inside the rectum, you can wind up hitting the rectal wall, which is not a good feeling for anyone. It sounds like that may be the sensation you described. Have your partner experiment with different positions and angles when he fucks you in the ass, and see if there’s one that allows for penetration without the pain. Toys made of flexible materials are more comfortable and bend easier with your curves; if a toy itself is curved, the curve should be aimed toward the front of the body. All that said, you can also have a short rectum. Since you get pleasure from wide toys, I say invest is some short but wide dildos or butt plugs — go with what works!

Ready to Blow Up

Feb 182005
 

Do you recommend using inflatable dildos to stretch the rectum?

–Ready to Blow Up

I don’t recommend anything to literally stretch the rectum. Toys are a great tool to teach the ass to relax and open up, to get it accustomed to being penetrated, and to warm up for more. It’s not stretching as much as it’s expanding, since the rectum has the ability expand when a person is turned on and relaxed. Inflatable dildos and butt plugs are a fun toy to play with, and they are also a great way to gradually increase the width of a toy you can take in your ass without investing in a new one. Make sure you inflate the toy before you put it in your ass to measure its limit, then you can gradually work your way up from one pump to several pumps!

Fellow Anal Lover

Feb 052005
 

I’m a 21 year old male anal sex lover. First off, I’d like to say that I respect your work a lot. It’s awesome that a woman like you does so much work to turn women on to accepting anal pleasure. With that said, here’s my dilemma. My girlfriend loves anal pleasure, but cannot handle it. When I finger her asshole, and or touch her pussy at all, she says it’s too much. She has to stop me because she says it feels too good, and that she can’t handle it. It is because of this we have never gotten past the two-finger mark. But she wants to have my cock in her ass, and, of course, so do I! I just recently ordered her some new toys, but my question is how can I get my girlfriend to relax? We think we have tried everything short of drugs, which we don’t want to try. How can I get my girlfriend to give in to the pleasure and loosen up? We both really want to get my cock into her ass without hurting her!

–Fellow Anal Lover

The ass is an incredibly sensitive erogenous zone, so it’s not surprising that some women can find anal stimulation or penetration too intense. Believe it or not, the more aroused your girlfriend gets, the more stimulation she’ll be able to take; blood will rush to her genitals and the entire area will get swollen and be more receptive to pleasure. Try to bring her close to orgasm before you play with her ass, and see if she responds any differently. If anal play still feels overwhelming to her, than you may want to investigate the situation further. Sometimes when a person is super-sensitive during sex, there may be an emotional component at work. One more tip: there are a few steps between the two-finger mark and your cock. One of the most common mistakes people make is that they rush penetration which leads to discomfort or pain. If you make it to a pleasurable two fingers, try adding a well-lubed third or try a small butt plug or dildo. When that feels great — and not before — you can consider your cock.

I’m In There, But Is She Into It?

Jan 172005
 

My wife seems to like the “naughtiness” of receiving my dick up her ass, but I don’t think she really likes it. We haven’t done it that much, but when we do, when I get it in there, she makes her sexy groan like when she’s going to come from a good licking. Part of the problem may be that we haven’t used much lube except her cunt juice. I don’t know if I really want to ask her if she wants to have it or not because she may say no and I don’t want to go there. Any advice on getting her more into it? We’ve talked about it outside of the bedroom, and she says she does it because she knows it turns me on and she likes to submit to my power over her. She’s very much in tune to her body and loves trying new things. Any suggestions?

–I’m In There, But Is She Into It?

Where do I begin? I’m disappointed to hear you have not been using any lube except cunt juice. Lube is a must for comfortable anal penetration, and no matter how juicy a cunt is, its fluids just won’t cut it. So, my first piece of advice is to get your hands on some lube and use plenty of it. You’ll be amazed at how much better it will feel for your wife.

From the information you provided — both about your conversations with your wife about her submissive desires and her response when you fuck her in the ass — it sounds like your wife does indeed enjoy your backdoor adventures. But the fact that you have avoided asking her directly because you “don’t want to go there” is a problem. Honest, ongoing communication is critical to any relationship and opening up a dialogue about anal sex with your partner can only be a good thing. You’ll get the answer to the question directly from her, and, if all goes well, maybe she’ll elaborate on some of those naughty, submissive fantasies of hers.

Ass-eating Cotton Mouth

Jan 132005
 

I am a newcomer to analingus, and I’ve only performed it on my girlfriend a few of times. Every time I do, my mouth gets extremely dry. Why is that?

–Ass-eating Cotton Mouth

As an avid ass-eater myself, I’ve never run into the problem you describe. But that doesn’t mean it’s not possible. There is nothing inherent to rimming that leads to a dry mouth, but there are a few possible explanations for your condition. As you lick your lover’s butthole and spread your saliva around, you may be sharing more spit than your mouth is producing, leading to an imbalance. You may also be dehydrated, which is easily rectified by drinking plenty of fluids before you dive back in. If it’s still uncomfortable, then I suggest you rub a small amount of lube (either a flavored one or one with a taste you don’t mind) on her pucker before you kiss it. Your dry mouth is most likely unrelated to your asslicking altogether: many medications can cause dehydrated mouth, as can common substances like tobacco, alcohol, and caffeine. If this parched condition persists, you should see your doctor.

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