Feb 202012

The Expert Guide to Pegging: Strap-on Anal Sex for Couples comes out on Valentine’s Day!! Isn’t that just perfect? My latest instructional movie from Vivid-Ed stars Dylan Ryan, Wolf Hudson, Jiz Lee, Mickey Mod, Jada Fire, and Christian. This is not your mama’s pegging video, that’s for sure! The cast is awesome, their interviews and chemistry fantastic, and the scenes are the hottest strap-on anal scenes I’ve ever shot! Plus, there are lots of extras on the DVD. And, as always, if you buy it directly from me, you support your local feminist pornographer!

Sep 272011

I’m a guy, and over the years, I have occasionally anally stimulated myself with my fingertip during masturbation. I recently convinced my wife to try a strap on with 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 prostate stimulation can cause ejaculation and orgasm. Even though we reached a point where a 5-6″ dildo was all the way in and being generously worked, I could get just to the edge of orgasm but not quite there. It felt incredible, but it was also a little disappointing. Is it a matter of working up to a larger dildo?

–On The Edge

You heard right: direct prostate stimulation can lead to a great deal of pleasure, orgasm, and ejaculation. The prostate is only a few inches inside the ass and toward the front of the body. With a 5-6″ dildo, you’re definitely going to hit it, and a longer toy is not the answer. You may want to try a curved dildo for more focused prostate stimulation (and aim the curved part toward the front of your body) and see if that makes a difference. If you have masturbated with anal penetration to orgasm, then the combination of the two may be what your body is most used to. Add penis stimulation as she fucks you to help you over that edge to orgasm.

Photo: Annie Cruz and Nomad in The Expert Guide to Anal Pleasure for Men

Nov 202004

I’m a guy, I like women, and I’ve never been attracted in any way to men. I want to try anal sex (with me on the receiving end) with dildos and even a strap-on. Does this action means I am gay? I have heard that men can have orgasms by prostate manipulation. How would my wife be able to do this to me? Is there a specific method or do I just hope that she does it right?

–Wanting But Wondering

The idea that men who like getting it up the butt are gay is absolutely a myth, one fueled by our society’s homophobia and misconceptions about anal pleasure. Plenty of heterosexual men enjoy receiving anal pleasure, whether with tongues, fingers, or toys. As I’ve said before, anal sex can be an incredibly powerful experience, but it’s not powerful enough to change your sexual orientation! I think that men who enjoy strap-on action especially have anxiety because of the implication that they are getting fucked by a cock, whether it’s silicone or not. The truth is that it feels good, and when you turn around, you want a woman on the other end of that cock.

Men can definitely have orgasms through anal penetration. The prostate gland is about an inch to an inch and a half inside the rectum on the front wall. So, if your wife slips her finger inside and heads toward the front of your body, she’ll find an area (about the size of a walnut) that feels differently textured than the rest of the rectal wall. She should gently rub the spot as you give her feedback about how it feels. Every guy is different, so your communication is critical to helping her stimulate you in exactly the way you want. As you get more aroused, the prostate will swell and become more sensitive. For prostate stimulation with a dildo (whether strapped on or in her hand), select a curved toy and make sure the curve is always toward the front of your body. Some guys like to have their cocks and balls played with, others want anal play alone — that’s something for the two of you to experiment with.

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!

Sep 282001

In one of your columns, regarding dildos and vibrators, you gave the following advice: “Just make sure that the vibrator is long enough like over 7″ for penetration, and, ideally, has a flared base.” While I can say from personal experience that a longer instrument is more satisfactory than a shorter one, real life does not treat you so kindly. My penis is 5 3/4 inches long, and the same in circumference, making it about 1.8 inches thick (when erect). In other words, short and thick. In fact 52 percent of men have an erect penis with a length of less than six inches. Only 4 1/2 percent of men have a penis length of 7 inches or more (My source is The Kinsey Report circa 1950). Therefore, I wonder if you could answer the following questions:

  1. Is a 5 to 6 inch penis too short to give adequate stimulation to your anal partner? Is it long enough to reach and massage the prostate with a male partner? Can it reach and massage the G-spot with a female partner?
  2. If, in fact, it is generally not long enough, are there any positions that are particularly recommended as shortening or compressing the anal channel to bring the sensitive surfaces within reach? Are they different for a male partner than a female partner?

—Short and Thick in Iowa

Well, you’ve obviously done your own research on the subject of anal pleasure, and you’ve given these matters a great deal of thought. While some people, both women and men, prefer a longer object in their asses, others are quite content with a member of your size. It’s really all a matter of individual taste, which is why one person might select a long, slender vibrating anal probe to bring herself to orgasm, but another person might choose something short and fat, like a robust butt plug, to push him over the edge. It just depends what you like.

Know that a 5 or 6 inch penis absolutely can stimulate a person’s ass just fine. Equally important, you can easily reach the prostate gland in men and the G-spot in women, since both “spots” are located just a few inches inside the rectum. In fact, I encourage most men who are using their cocks to stimulate the G-spot not to penetrate fully, since you’ll slide right by the G-spot (the same is true for the prostate).

As for positions, putting the receptive partner in doggie-style position (or what I call modified doggie style, where the head is down and the ass is in the air) can afford you a perfect angle to hit the G spot or the prostate and give you the opportunity for deeper penetration. You cannot actually “compress the anal channel,” but you can get in there deeper at that angle.

As for the differences in male and female anal anatomy, our anatomy is nearly identical except that men have a prostate gland (which can be stimulated through the rectum) and women have a G-spot (which can be directly stimulated through vaginal penetration and indirectly stimulated through anal penetration). Please don’t feel like your cock is inadequate, Short and Thick; as long as you know how to use it, you can bring your partner plenty of pleasure.

Jul 182000

I would really like to have my wife perform anal pleasure on my ass but she doesn’t seem to be very into it. She enjoys receiving anal sex, and I have mentioned in the past what I would like her to do, but I can tell she’s a little weirded out by my request. Any suggestions?


Congratulations on coming out of the backdoor closet! I think it is especially revolutionary for straight men to admit their desire to be the receivers of anal pleasure. You join plenty of men who want to get done in the ass, and I promise you that once you’ve had your prostate gland stimulated, you’ll never be the same again! For men, it’s a chance to be penetrated, to give your body over to a woman in a new way. Seriously, I think every man should be fucked in the ass at least once in their life, and I am so glad you are ready to try it. I truly believe that getting fucked in the ass is one of the greatest gifts you can give a woman and yourself.

Now, on to your wife. I am not sure exactly why she is “weirded out” by your request. I can tell you that she doesn’t know what she is missing. Giving men anal pleasure gives women an opportunity to be the aggressor or the penetrator for the first time. Your wife has the chance to experience her sexual power as a woman and a giver of pleasure in a wholly unique way. Have you asked her directly why she might be hesitant to do it? Many people can buy into the myth that if men want to be fucked in the ass, then they are really gay. This is ridiculous, of course. Because anal sex is falsely linked with gay men and gay sex, there is a myth that if men want anal sex, then they must be gay. In most cases, men who identify as heterosexual and desire giving and/or receiving anal sex with women are not repressing homosexual desires or tendencies. Their desire for a particular sexual activity does not rely on or “cancel out” their sexual preference in a partner. According to research, more gay men regularly practice fellatio than anal sex, and as my friend Audrey says, “How come no one ever asks: if a straight guy likes blow jobs, does that mean he’s really gay?” Your wife may be a victim of this stereotype, and you need to assure her that you love her, are attracted to her, and want her to do you in the ass.

Different men also want to be fucked in different ways. Some want to be submissive as part of an SM scene, and giving up your ass can be an ecstatic way to submit. Men have lots of issues to get over when it comes to being penetrated (feeling passive, receptive, plus homophobia), so sometimes being “forced” to do it by a Mistress or dominant woman helps them take that leap. These are specific to SM, and may or may not apply to you. Either way, men don’t necessarily have to be bottoms to be fucked in the ass. I have personally fucked plenty of tops in the ass without flipping them — it’s all in the way you play it.

There are a few superb resources that I recommend you and your wife check out. They will help to open up a dialogue about this subject, and will also give you great information, tips, and techniques for doing the deed. The book, The Ultimate Guide to Strap-on Sex by Karlyn Lotney is informative and very useful. There are two videos: Bend Over Boyfriend is heavy on super instruction and stars real life couples. Bend Over Boyfriend 2: Less Talkin’, More Rockin’ has a title that says it all. Both are produced by S.I.R. Video.

Mar 081999

I have just started working as a professional dominatrix, and some of my clients (men) want me to fuck them in the ass with a strap-on. Any advice for a novice in that area?

–Mistress Scarlett, Minneapolis, MN

I am so glad you brought this subject up! I just went to a play party at a small dungeon, and watched an amazing anal scene. A tall, gorgeous dom with fiery red hair and thigh-high PVC boots had her sub on his knees sucking her strap-on cock with his hands tied behind his back. He was a little wisp of a thing, but boy could he fit that big cock in his mouth. After he serviced her, she put him on a bondage table on his back, and basically tied his knees to his chest with some beautiful rope work (red, of course). When she snapped on a latex glove, you could see his eyes get big and glassy. She started working her fingers in his ass, and he squirmed and moaned, but couldn’t go anywhere. She came to the edge of the table and started teasing him with her greased-up cock. He went nuts. Finally, she gave it to him, all eight inches, and he was in heaven.

Now for my advice:

There are so many men out there who enjoy having their assholes stimulated, played with, licked, and penetrated. And, according to lots of men I’ve talked to who are into power play, they especially love to be anally penetrated as part of being dominated, disciplined, even punished or humiliated. In addition to all the nerve endings in the anal area, men have a pleasure spot that’s just too good to overlook — the prostate gland. You can stimulate the prostate with your finger or a dildo.

First, you want to choose a harness that fits you well — the snugger and more secure the better; there are many different kinds (usually made of nylon or leather), and you should definitely try them on in a sex toy store if possible to see which works best for you. For beginning anal players, I would recommend a smaller dildo to start out, but of course, you should find what works best for you and your clients.

As the one doing the penetration, you should also experiment with different positions. I know that the first few times I fucked someone in the ass with a strap-on, I had the person in traditional doggie-style position for several reasons: 1) doggie style gives you a clear view of the butthole, so you can see what the hell you’re doing 2) the position allows for a good angle of penetration, towards the prostate in men (and towards the G-spot in women); and 3) it’s an easy angle to get your balance, establish a rhythm, and get some good thrusting going. So, you may want to start out that way, but you can also try missionary (usually with legs over the shoulders) or man-on-top. Although, as a dominant, I would say that putting him in a position with his ass in the air and head down is probably the best way to go, both practically and for its obvious submissive possibilities.

Anal penetration requires patience, practice and lube, lots of lube. Make sure your bottom is warmed up with lots of teasing. When you start out, you want to go slow and let the butt get used to having something inside it. Always work your way up, adding more lube as you go. When he’s finally read for that big silicone dick, be gentle at first; the more you go easy in the beginning, the more his ass will open up and trust you later on when you really want to ram the guy!

For more on this subject, definitely check out the fabulous video series: Bend Over Boyfriend (Fatale Video) and Bend Over Boyfriend 2: Less Talkin’, More Rockin’ (S.I.R. Productions). There is also a good book called The Strap On Book (Greenery Press) and another called The Ultimate Guide to Dildo and Harness Sex (Cleis Press).