Ready for An Overnighter

Aug 202002
 

My wife and I both enjoy extended anal sex. One of our favorite things to do is to put an X-rated movie in the VCR, lube up, hook up, and watch the whole thing start to finish. I usually cum at least once, regularly more than once. A couple of times lately, one or the other of us has fallen asleep before the movie ends. Not wanting to wake the sleeping one, whoever’s awake just hits the power button on the remote and takes a nap. When the sleepyhead wakes up after an hour or so, we separate, shower, and go to bed.

We’ve been fantasizing about just staying “connected” until it’s time to get up the next morning. I don’t seem to have any problem with a priaprism (prolonged sustained erection), as her anus is fairly relaxed the whole time. My cock goes from nearly flaccid to nicely erect once every ten minutes or so while we’re connected, reportedly even when I’m the one asleep. We both like deep anal penetration, and keeping my cock in all the way to the base probably also has something to do with good blood flow out.

So, should we go ahead and spend the night locked in an anal embrace? We’ve tried this vaginally, but the lack of a sphincter muscle means that when I go limp I fall out. Her anal sphincter, and the vacuum effect of such a tight seal seems to be just enough to prevent that from happening during extended anal sex. Also, we’ve found a position (spooned, with both my legs wrapped around her bottom leg — impossible on anything but a waterbed), that keeps the penetration deep enough to help hold me in.

–Ready for An Overnighter

I must commend you on one of the most creative letters this Anal Advisor has ever received! It sounds like you’ve already experimented with staying inside her ass during short naps, and it’s worked pretty well. It sounds like you are blessed with the ability to go from soft to hard fairly easily, which definitely makes the situation easier. I am impressed that neither one of you moves during these naps, which would certainly break the connection.

As for trying this for an entire night of sleep, I am not so sure it’s a good idea. First, surely one or both of you will shift during the night, which could result in an awkward position or worse, you could hurt the other. Second, I can’t imagine that for several hours you’ll be able to maintain an erection (even for ten minutes at a time), which will make prolonged penetration very difficult. Third, if you did achieve the kind of “vacuum,” as you called it, the risk of cutting off or decreasing the circulation in your cock is too great. Hey, you’ve made these catnaps work, which is more than most people can do, so I say, keep having those short, fun encounters and don’t be greedy!

Wants Her Ass Open

Aug 112002
 

My girlfriend and I love your book, love your movies and love anal sex. We’ve been fascinated by the ability of some porn stars to hold their anus open after having anal sex. My girlfriend would really like to be able to do that I would love for her to. Are there exercises she can do to achieve this? How can she learn to stay open after we have anal sex?

–Wants Her Ass Open

In the adult industry, the post-fucking state of openness of an ass which you refer to is called “the gape,” as in the popular vid series Planet of the Gapes. People write to me about seeing the gape in porn videos all the time, but usually it’s in fear. In other words, most folks see a nice, wide open ass and panic; they think that once they have anal sex, their ass will end up like a giant pink hole, they’ll lose control of their bowel movements, and the anal sphincter muscles will forever stay open. Of course, this isn’t the case. I often reassure people that what they are seeing is the ass “at play” — it’s just had something quite big pounding away at it, so it’s naturally very relaxed, aroused, and ajar. If you saw the same asshole “at rest,” it would be small, closed, and puckered as usual.

Your question is an interesting one because you and your girlfriend want to achieve the gape, whereas most folks are freaked out by it. In my experience, some women gape quite easily, others gape only after a prolonged intense assfucking, and others rarely if ever get a gape going. Some of it is pure chance; it has to do with how the body responds to penetration, and in particular how the ass behaves after prolonged stimulation. I don’t think there are any exercises your girlfriend can do to improve her chances of gaping. But she may want to try a few tricks to see if they help keep her ass open. After you pull out, she can reach around and spread her ass cheeks with both hands, which will give the illusion of an open ass. Have her bear down slightly; this may loosen the sphincter muscles and keep them from closing back to their puckered state. You may also want to try putting a butt plug with a wide neck in her ass; this helps relax and open the muscles. The best you can do is practice, and see what works best for both of you.

Did A Boo Boo

Jul 242002
 

My boyfriend and I have just started having anal sex and I really love it. But recently we went from ass to pussy for the first time and now I’m feeling a lot of discomfort in my pussy. I just read one of your answers to a letter about that and you said that it wasn’t a good idea in case of infection. Now that I’ve already done the mistake is there anything that you recommend in order to soothe the discomfort in my pussy? Any over the counter drugs or natural remedies?

–Did A Boo Boo

By the time you read this letter, I am sure my advice will be a little late; however, I think many women may have similar experiences of accidental ass to pussy penetration, so it’s worth addressing. Going directly from ass to pussy is never a good idea because there is bacteria that lives in your rectum that, when introduced into your pussy, will more often than not cause a problem. It may result in a yeast overgrowth or imbalance, a urinary tract infection, or a vaginal infection like Gardinerella.

Immediately after sex, I would take the following steps. Pee, even if you don’t feel like you have to, in order to flush out any bacteria which may have gotten lodged in your urethra. Drink lots of water to also help flush bacteria and other toxins from the body. Shower and wash your genitals with castile soap in order to clean out what you can. I recommend castile soap rather than anti-bacterial soap or other bath soaps because the latter types can often encourage the growth of bacteria and yeast. You may consider douching, but that’s not a good idea. While douching can rinse the pussy, it can also push some bacteria further back into the vagina, where it can breed. These may lessen the chances of a problem, but I don’t recommend that any woman attempt to self-diagnose a vaginal infection.

To soothe the discomfort, you can purchase external creams or soothing wipes with witch hazel at any drug store. If you exhibit any symptoms, though, including itching, burning, redness, irritation, abnormal discharge, or pain, you should see your gynecologist as soon as possible.

Preggo Anal-Addict

Jul 052002
 

Me and my partner have always enjoyed anal sex. We have been together for a while and are expecting our first baby in three months. I know people are supposed to have “cravings” when they are pregnant, but my craving is that I want to be fucked in the ass even more than I did before! It feels great, and I experience no discomfort, but we want to make sure that we aren’t doing any harm to the baby (and I don’t exactly feel I can discuss it with my doctor!). I find the most comfortable position is on my knees with my butt sticking up so I can support my belly properly, and this way I can get the most cock in my ass. Will it be alright to continue up to the time you would normally stop having vaginal sex?

–Preggo Anal-Addict

Many women say that their libido, sexual tastes, and orgasms can change drastically during pregnancy, so know that your new craving is perfectly natural. According to most physicians, throughout your pregnancy, penetration (both vaginal and anal) with fingers is safe and with a cock is safe in low-risk pregnancies. One of the challenges of sex during pregnancy is finding comfortable positions, and it sounds like you’ve found a good one, at least for now — it may change when you get bigger. Your mate should definitely avoid deep thrusting and really hard slamming of any kind. Use a water-based lubricant, but be extra careful in preventing bacteria from the ass transferring to the vagina. Make sure his fingers and cock are super clean, or you may get an infection, which is often harder to treat during pregnancy. If you feel any discomfort during any sexual activity, stop at once. You said you don’t feel comfortable talking to your doctor about this, but for the sake of your health, and the health of your baby, it’s probably a good idea.

Rash From Her Ass

Jun 142002
 

I recently started dating, well, fucking, somebody I’ve known for close to a year. She has been without a sexual partner for a long time, but she’s a serious hypochondriac about STDs; she was tested for everything twice in April, and once last month. She gets depo shots, so we fuck without condoms (don’t worry, we do use lube). So, how come I get a strange rash on my glans and foreskin, usually lasting for a day or two, when I fuck her in the ass? It doesn’t hurt and it basically just makes the regular bumps and pores looks bigger and red. There’s no funky smell or discharge either. I’ve studied the symptoms of about every friggin’ STD more than this girl has, plus I’ve been tested more than she has. It doesn’t look like any STD I’ve heard of.

–Rash From Her Ass

I know you think your lover is a hypochondriac, but I applaud both of you for getting tested often because most people do not. And it also sounds like you know a lot about STDs, which makes you more educated than the average fella on that subject. I have a few theories about the rash on your cock. My first one is that you may be having an allergic reaction to the lube you are using. Most lubes, whether water-based or silicone-based have similar ingredients, but they are not all the same. Personally, I got a red, itchy pussy from one particular brand of lube that I was trying out for the first time. I never used it again, and I haven’t had the symptoms again. So, try using a different brand of lube and see if that changes anything. You could also go to your doctor when you’re having symptoms to get a full examination and see what he or she has to say. It sounds like you know a lot about STDs, but it’s always better to be safe than sorry.

Booty Lover

Jun 072002
 

My girlfriend and I have been having anal sex for about four or five months. In fact, the first time I penetrated her was anally. After that, it’s been a once-in-a-while ritual where I get to have the pleasure of making love to her sexy ass. I enjoy it very much and she doesn’t mind letting me have my way, even though she says she receives little to no pleasure from it. We use plenty of lube and always warm up with shallow and slow penetration, deep breathing and lots of communication. We now do it now once every three weeks to a month, which is kind of my problem. I’d like to do it more often, but not too much.

I have two questions for you: How much anal sex do you think is healthy for a couple that wants to have a nice balance between the three major forms of sex (oral, vaginal and anal)? What kind of ways can I pleasure her when I do her in the ass? How can I make her come from anal sex?

–Booty Lover

There is no mathematical equation to determine “a nice balance,” nor is there any common recommendation about how much of one kind of sex a healthy couple should have. Sexuality and our particular practices are extremely unique to the individuals involved, and therefore so are our preferences and how often or little we indulge in them. I say if both you and your wife are content with how much sex you’re having, and the kinds of sex you’re having, then why mess with a good thing?

But it does sound like you’d like to add more anal sex to the menu, and your second question is the key to getting there. Because if you start to give her tremendous pleasure while you’re fucking her in the ass, then chances are she’ll want to do it more often. There are a number of ways to get a woman off while you’re fucking her ass. You can play with her clit while you penetrate her, or if the position you’re in makes that too difficult, encourage her to jerk herself off or even use a small vibrator. Clitoral stimulation combined with anal penetration is one of the ways some women can orgasm. If she likes double penetration, try putting a few fingers in her pussy or a slim dildo while you’re in her ass; this often increases the sensations in both places. Experiment with different positions in order to find her G-spot. Many women experience indirect G-spot stimulation through anal sex. You want to angle fingers, toys, or your cock toward the front of her body to find and stimulate the spot. Also, ask her what she’d like to do to make it feel not just better, but fantastic. Together, you can discover what will turn you both on.

Anal Chicken

May 282002
 

My husband and I want to try out anal sex really bad, but my problem is the pain — I know it’s not supposed to hurt, but it does. I keep telling him that missionary position is not the best for our first try. Is there another position you recommend? I really want to give this to him, but I am still very nervous. I have tried to relax, but nothing seems to work. I’m thinking I need a lube that desensitizes the area. I know if I can find the right kind of numbing agent, then I will do just fine. Do you know of any?

–Anal Chicken

You admitted being nervous about getting fucked in the ass, which is very common, but my question is: do you really want to do it? I sense a lot of reservation in your letter, and I am concerned that your fear and anxiety aren’t the only things holding you back. Your desire for this must absolutely be there (not just your husband’s), otherwise it’s not going to work, and it will continue to hurt. You are right that it is not supposed to hurt, and pain can be the result of many things: hesitation on your part; not being relaxed; not enough foreplay and warm up; not enough lube. You need to take it slow, and have him open your ass with fingers or small toys before he even attempts to put his cock in there.

As for positions, if missionary isn’t working for you, trust your instincts. Maybe you should get on top, so you can control the depth of penetration, the speed, and you can move your body to get the best angle. Or you could try doggie style, but make sure he doesn’t thrust all the way inside on the first time around.

I cannot recommend any of the de-sensitizing lubricants that are available. Numbing your ass just isn’t a good idea. If you can’t feel anything, you cannot listen to your body’s warning signs that things are going too fast, and you’ll most likely end up with a sore butt the next day. Plus, if it’s numb, you can’t feel all the pleasurable sensations that anal sex can give you, and trust me, you want to feel those.

Slick for Starch

May 162002
 


I recently read that someone made a dildo for anal penetration using pureed mashed potatoes stuffed into a condom which was tied at the end. I would like the instructions for such a device.

–Slick for Starch

Not only is this self-made dildo dangerous for anal play—since there is no flared base or string attached, and a condom isn’t very long, it can easily get lost in your ass—it doesn’t even sound like that much fun. Between the mess it will make putting it together (unless you’ve got some serious kitchen utensils) and the mushy texture it will have when it’s done, I am not very intrigued. Please splurge and buy yourself a dildo or butt plug at a sex toy store. Trust me, you’re worth it.

Mistress Mean

Apr 182002
 


I’m a professional dominatrix, and have several clients into forced feminization and anal play. Some of them have requested that I insert tampons into their (anal) “pussies.” Can this be done safely? I know that there is a risk of toxic shock syndrome when tampons are used vaginally, and I am wondering if it can happen in the ass as well.

–Mistress Mean

Toxic Shock Syndrome is a blood-borne bacterial infection caused by the bacteria Staphylococcus. We most commonly hear about it in relation to using tampons, and symptoms can include fever, chills, vomiting, sore throat, headache and more serious conditions. It is treated with intravenous antibiotics to prevent shock and kidney failure. TSS colonizes skin and mucous membranes, and the rectum is a mucous membrane; however, I had a difficult time locating any documented cases of TSS through the use of tampons anally. Since tampons are used to absorb moisture, it could be uncomfortable and dehydrating at the very least.

I have an easy solution for you. In fact, it’s for anyone who has a client lover who wants something in his or her ass which you know is either unsafe or potentially dangerous (other examples include glass bottles, candles, baseball bats, just to name a few). Find a sex toy with a similar size and feel to the desired (but unadvisable) object. Blindfold your bottom before inserting the toy in his or her ass, and make sure to talk about whatever the fantasized thing is in great detail. If you’re a good Top, you can convince a submissive of almost anything.

Anal Slut in Texas

Apr 042002
 


My partner and I are in a permanent Dominant/submissive relationship, and have been experimenting with anal sex for over two years now. We both get a lot of pleasure out of it. He likes to have me wear a locking harness to keep a butt plug in place while we go out to dinner and a movie. The trouble is, after about an hour, I need to use the restroom and must remove it. What can I do prior to ‘harnessing up’ that will allow me to be able to wear the harness for a longer time? Should I change my diet prior to the excursion?

—Anal Slut in Texas

The amount of time you can wear a butt plug depends upon your personal bathroom schedule, and everyone’s particular time table varies greatly. It sounds like you’re an evening bathroom goer, and that you’ve got a pretty fast metabolism (because shortly after eating, you have to go to the bathroom). In order to prolong your butt plug wearing, I suggest that dinner time be moved. You could eat dinner, wait to have a bowel movement, then get locked in your harness for several hours. Or perhaps you can have an outing with the butt plug in your ass that doesn’t involve food, then, after the scene is over, treat yourself to a meal. If the outing must include dinner, than perhaps your Top should insist that you watch him eat, while you’re limited to water only (sorry to give him tips from my sadistic Top self, but you did ask). If you’re a good girl, maybe he’ll feed you after you’ve held that butt plug in long enough!

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