Waiting to Come

Aug 052004
 

I am a heterosexual married man, and I have been occasionally stimulated myself with a finger during masturbation for years. I recently convinced my wife to try a strap on a dildo and fuck me. As I expected, I enjoyed both the physical stimulation and the psychological joy of giving myself up to her as the penetrator. But try as we may, the buttfucking could not get me to orgasm. I have heard that direct prostrate stimulation can cause orgasm and ejaculation. But for me, even though we reached a point where a modest, 5-6″ dildo was all the way in and being generously worked, I could get just at the edge of orgasm but not quite there.

Not that I’m complaining, because the whole encounter was great. If I was at the same point of arousal and pleasure as I was fucking my wife, I couldn’t have held back. But anally, to put it bluntly, I was able to be buttfucked at that same pinacle of near orgasm delight for as long as my wife could go and I could take NOT coming. The whole time it felt like “just a little faster, or harder, or deeper and I’ll come.” It was incredible, but also disappointing. Am I going to have to have my penis stimulated to get an orgasm, or is it a matter of working up to a larger dildo to hit the prostate?

–Waiting to Come

Before I answer your question, thanks for your testimonial about the joys of being buttfucked by your wife; I hope it serves as an inspiration to all your hetero-male bretheren! This is not a problem of size, I can assure you, because the prostate is just a few inches inside the rectum, so something bigger or longer is not going to solve this quandary. First, I want to encourage you to add cock stimulation to the mix since guys like to be stimulated in both places at once; try working your dick as she fucks you and see if the result is different. Second, you may experience a different kind of orgasm from prostate stimulation than you do from having your penis stimulated manually, orally or via penetration. Many men report that they have all the sensations of an orgasm without ejaculation. So, it may be simply a matter of re-orienting your mind around a different expectation of an orgasm. Third, you may still be able to come and shoot from a good assfucking, and in that case, practice makes perfect!

Burned Butt

Jul 282004
 

I’ve had a black vinyl butt plug for two years and I think that a chemical film or something has developed on the surface that makes it burn when I insert it into my girlfriend’s ass. Would an automotive-type vinyl restorer make my butt toys last longer?

–Burned Butt

Latex rubber, jelly rubber, and vinyl sex toys are inexpensive for a reason: they do not last forever. I recommend that folks replace toys made of these materials after twelve months for the exact reason you report: the material starts to break down, and often causes stinging, burning, itching, and other discomfort when used.

No, a vinyl restorer sold in automotive supply stories is not a good idea; not only will it not help stop the toy from deteriorating, but you do not want any product like that (or traces of it) in your ass! Throw the toy and buy a new one, or, for your next purchase, try a higher quality silicone toy. Silicone can be much more pricey, but it’s also a lot more resilient. My silicone toys have lasted for many years, and some brands even come with lifetime guarantees.

Enema Edge Player

Jul 142004
 

I bought a simple Fleet enema at the drugstore, and I have a few questions. Can I use it as is, or should I replace what’s in the bottle with water? Here’s why I am asking: I like to experience some good hard erotic cramping during enema play. My girlfriend and I often do enemas together, and we like to see which one of us can hold it the longest and who can handle the cramps without showing much discomfort. Is that safe? Because it’s awfully fun.

–Enema Edge Player

When I teach a basic class on enemas, I instruct people on two important points: the ingredients of an enema and the temperature. A Fleet enema (or most other brands you buy at the local drugstore) contains a laxative, and you do not need a laxative. You just need plain, warm water, which is why you should empty the contents of the store-bought enema bottle, rinse it out and refill it with warm water. If you’ve heard of more exotic enemas, with ingredients like champagne, espresso, wine, or other things, beware: these can make you very, very sick. So stick to plain water only.

I recommend that the water be warm so it’s as close to body temperature as possible; usually, the warmer the water, the more comfortable the enema. Most people will have little or no cramping when the temperature is right. Cold water causes discomfort and cramps that most people won’t like. I say most people because I do know enema fetishists who like to deliberately inflict discomfort and cramping on themselves or their partners.

Let me first say that this is considered “edge play” among enema fans, and inexperienced enema givers and receivers should not try this at home. I can tell that you’re a much more seasoned enema player, so I won’t admonish you for your sadomasochistic twist on this intimate form of play. One word of caution: don’t overdo the cold-water, cramp-inducing sessions. You can stress your gastrointestinal tract and disturb the delicate balance of your insides, which is never a good idea. As for you and your partner’s little game, it sounds like a great endurance contest for the BDSM Olympics! Again, a good rule of thumb for all this kind of play: everything in moderation.

Going for the Gape

Jun 302004
 

I am a thirty year old woman in a D/s relationship. My Master really enjoyed something that I unknowingly did last night. I was in “doggie style” position, and he was playing with my ass from behind. I was very, very aroused and without knowing or trying, I experienced what I have seen you refer to as “the gape.” It turned him on a great deal. I was able to continue this for quite while, even while alternating contracting and relaxing my sphincter muscles. Then, suddenly, I just couldn’t reproduce the gape again no matter how I tried. If you have any information on how I might cultivate or encourage this skill, I would be most grateful.

–Going for the Gape

It sounds to me like you stumbled upon something that other people work pretty hard to achieve! Usually in order to get the gape, you need to be very turned on (as you said you were) and have an extended anal penetration scene to get your sphincter muscles to relax and open up. For some women, having something sizable in their ass for a while is enough to bring on the gape. From the description of your experience, you have a good awareness of and control over those muscles, which can also help you go for the gape. In addition to trying to contract and relax the sphincters, you may also want to try to bear down slightly, and see what effect that produces. Continuous penetration of some kind may be the key to extending the gape for you, since it sounds like, at some point, the banging stopped, and you were just flexing your muscles. If your Master continues to play with your ass, thus stimulating the area, I bet you’ll be able to extend the gape.

Mistress of His Ass

Jun 152004
 

My boyfriend is ultra submissive in just one area: his ass. He doesn’t go for the Mistress thing, lick-my-boot mentality, but when it comes to his ass (which is the focus of his fantasies and always how he’s able to come) he’s full sub. I know exactly what he needs that way, pain and humiliation. Directed at his ass. Insulting HIM gets us nowhere, but insulting HIS ASS does. My snag is this: there are only so many ways to insult an ass. Degrading his ass, calling it a cunt or pussy gets him off in a snap. Is there any way to get good ideas to boost my imagination so play is not monotonous for either of us?

–Mistress of His Ass

Plenty of people get off on pain, humiliation, degradation, and overall submission. Clearly your boyfriend’s submissiveness is tied directly to his ass and anal play. There are many ways to combine submission and anal pleasure. You’ve already insulted his ass, but have you also tried to insult and humiliate him for wanting his ass penetrated, for being a naughty butt boy? Take all the cultural baggage that comes with anal pleasure, and use it to your advantage, as a psychological tool: it’s dirty, taboo, dangerous, and will make him gay. Of course those aren’t true, but these myths can make for great mindfuck material.

If he likes extreme submission, you may also want to explore forced anal penetration or anal rape scenes; that’s tricky territory, so tread lightly. It also sounds like there is an element of gender play in your man’s fantasies, since he enjoys having his ass be called his pussy. Try to explore that part of his desire further. Does he want to crossdress, to be girl? Does he want to be forced to do it? Forced feminization is quite popular and may be part of what he’s try to express in the anal play you’re currently having. See if he will open up about and be specific about his submissive anal desires, and use what he gives you to take things to the next level.

Wanting More

Jun 032004
 

As long as we do lots of foreplay and my body is prepared, I don’t have a problem with pain during anal penetration. However, after about four inches of cock in my ass, I get abdominal pain that I can’t get past, no matter how relaxed or aroused I am. We’ve tried changing positions, but no matter what, it’s as if there is a road block. This is frustrating for me, and I know that for my husband, who wants his balls to slap my pussy on the downswing, it has to be downright maddening. I asked a girlfriend who’s into anal if she had ever experienced this, and she says that around the seven inch mark, her guy seems to hit a wall. Is it possible that there is a sharp bend that is preventing full penetration? Is there a technique to get around the discomfort I am experiencing? Swing to the left? Swing to the right?

–Wanting More

The first two inches inside the anus is called the anal canal, and the rectum is the area from the anal canal to the colon, which is another five to seven inches. Unlike the vagina, where you’ve got a pretty straight shot from end to end, the rectum is curved. That’s especially important to know when penetrating someone’s ass with anything longer than a finger, and especially with a dildo or vibrator that is firm and inflexible (like one made of hard plastic, clear acrylic, or glass). If you jam something (especially something rock hard) straight inside you can absolutely hit the rectal wall, which does not feel good. As you get more turned on, the rectum expands, and the curves are less pronounced, but they are still present.

So, the “four inch” stopping point you describe could correspond with the first curve of the rectum, when it curves toward the front of the body. Everyone’s internal geography is unique, and it’s possible that your rectum is more curvy than others. I’ve heard people report similar feelings of facing a roadblock inside their asses.

You’ve already tried changing positions, which would be my first suggestion. I suggest that you pick a long, very flexible toy, and, while masturbating, begin exploring your ass with it. Take note of the curve of the rectum, what feels good and what doesn’t, and if you can find your roadblock, or if you develop discomfort. Experiment with moving the toy forward or back inside of you to see if that changes anything. If you can find the trouble spot, see if you can move past it or around it, again, by moving it toward the front of the body or toward the back. If you are still experiencing problems, I suggest you talk to your doctor about it and have a rectal exam.

Bun Lover

May 202004
 

Is butt cheek fucking, or what is sometimes known as “hot dogging,” a common practice? I know tit fucking is quite common but I’ve never seen much talk of cheek fucking. Why do I never read about it in magazines or even see anything about it on the internet? Is it something that turns women off? Have you ever tried it? If so, did you get anything out of it? Let me know if you have come across it, and what your opinions are.

–Bun Lover

You’ve hit on something here, Bun Lover: there are plenty of erotic images of cocks sliding between breasts, but little or no comparable representations of hot dogging! I suspect that in this age of porn featuring a veritable menu of Olympic-like sexual acts (like double penetration and double anals), butt cheek fucking is probably seen as far too innocent. Certainly we’ve seen dicks slide between ass cheeks, but it’s usually a brief shot before penetration. As for the “turn on” factor you asked about, well, just like with every other desire, fantasy, and fetish, it totally depends on the person. I actually do enjoy it, but I may be more anally-inclined than the average girl. Sometimes, I like butt cheek fucking as a tease; other times, if I am craving anal pleasure but my ass isn’t in the mood for penetration, butt cheek fucking along with some good dirty talk can totally get me off.

Questioning Her Anal Love

May 122004
 

I have been with my girlfriend for six years, going on seven. The sex is really amazing, but something is missing: anal. I love to eat her pussy a lot. The taste of her and just being down there can make me come. For the past year, when we 69, as I lick her pussy, I have been playing with her ass, and she moans louder when I do that. One time, my whole thumb was in her ass and she loved it. But when we talk about it, she seems hesitant. When I go down on her, I tend to give her a small rim job. Or, when we are in missionary position and I swivel her left leg over so her ass is exposed and play with her ass. She gets into it, and then stops. I’m very confused. I think she loves it, but I don’t know.

–Questioning Her Anal Love

It sounds to me like you two need to have a conversation about anal pleasure. According to your account, your girlfriend isn’t opposed to it, though it seems that you want to go further than she is comfortable going. It may be that rimming and penetration with a finger feels great, and she has no desire to do any more. But the fact that you’re getting mixed signals means she may have some unexplored issues that prevent her from fully enjoying the anal play you already do and stop her from further exploration. Be open, compassionate, and non-judgmental when you approach her. Ask her if she has fears or misgivings about anal pleasure; she may have concerns about hygiene, safer sex, penetration, and other common issues associated with butt sex. Talk through these issues, and see if you can get to the bottom of her feelings.

Big E

Apr 252004
 

I’m 29 years old, and I have been putting things up my ass for about ten years now. I’ve worked my way up to take equivalent of three cucumbers. The last time I put things up my ass, the most bizarre thing happened, and it’s happened once before about a year ago. I like watery vegetables because I feel like I need less lube and my ass gets a “wet silk” feeling from them. After I inserted a peeled cucumber, I had this allergy-like reaction all over my body. The same thing happened last year with a carrot. Nothing grave, just red, itchy, swollen eyes etc. which went away in about an hour. I know what it is since I’ve been allergic to lots of stuff since I was a child and still have serious hayfever. Is it the absorption of the vegetable juices by my rectum that causes the allergy or something else? Any knowledge of anybody experiencing this, or what it could be exactly? I mean, one does not want to go into anaphylactic shock with a set of cucumbers up one’s ass, right?

–Big E

If I have told you once, I’ve told you a million times: leave the vegetables in the kitchen and out of your ass! Of all food allergies, allergies to vegetables are not as common as others, however there is some research which shows that certain foods — including melon, banana, zucchini and cucumber — as well as the popular herb chamomile, can aggravate ragweed allergies. Symptoms include itching and tingling of the mouth, lips, throat, and ears, and in more serious cases, the swelling of tissue or anaphylactic shock. You said that you have allergies and hayfever, so my guess is that’s you’re allergic to ragweed, and some of the vegetables you’re sticking up your ass are exacerbating this allergy. One more example of why you should stick to silicone, rather than organic, phallic objects!

Double Dildo Dilemma

Apr 172004
 

I was hoping to get some of your good advice before purchasing a strap-on to fuck my girlfriend in the ass. I came across one called the “double whammy”, a two-headed dildo which has one long shaft to insert in the recipient and another shorter shaft to insert in the wearer of the strap-on harness. This enables the one doing the fucking (me) to feel some penetration herself and thus enjoy the whole thing a little more. Have you in your years of experience come across one of these things and if so are they any good for either partner? What does it feel like for the wearer? Can the wearer really get off while fucking the other person?

–Double Dildo Dilemma

Most double ended dildos are just like one long dildo with two heads, and, while they can be fun for partners to share, they can’t be used with a strap-on harness. The toy that you described sounds to me like the Nexus, a silicone double-headed dildo from Vixen Creations that was designed specifically for use with a harness. One end sticks out of the harness for fucking your girl, and the other slips inside you. As you thrust with your hips to push the dildo inside your partner, the other end penetrates you. The Nexus is a totally unique toy, and one that lots of people rave about; I’ve used it myself and really like it. It comes in two sizes, and is ideal if the size of each dildo works for each partner.

As to your question, “Can the wearer really get off while fucking the other person?” Well, that all depends on how the wearer gets off! For some women, wearing a standard (not two headed) dildo in a harness is very arousing since as you start thrusting, the base of the dildo can rub up against your clit. Also, there are vibrating dildos that can be used in a harness, to give the wearer (and her partner) plenty of buzz where it counts. If penetration is what gets you off, and the Nexus hits the right spot, then it can add a whole new level to your strap-on pleasure.

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