Fill My Ass

May 092001
 


I like to have objects in my ass while I masturbate, but I don’t have a dildo. What kinds of household objects can I use to simulate a penis?

—Fill My Ass

There is a reason that household objects are household objects; they each have a purpose, and it’s not sexual. I am thrilled that you’ve discovered anal penetration as part of your masturbation ritual, but I really don’t want to encourage you to grab the hairbrush, the shampoo bottle, the cucumber, or anything else lying around. Has it been done? Of course, but I don’t condone it usually.

I really recommend that you buy a dildo. You need something with a flared base for anal penetration; it’s an absolute necessity, so the object doesn’t get sucked into your ass or lost somewhere in your rectum. Sex toys were manufactured with sex in mind, they are designed for penetration, and therefore much more ideal for it than a makeshift dong. There are relatively inexpensive dildos on the market, especially the rubber or jelly variety (silicone dicks are much more expensive). But yourself a $15 or $20 dildo, and I promise it is well worth the investment.

Butt Plug Beginner

Apr 102001
 


I, like you, totally love anal sex. I have played with dildos and vibrators, and had lots of fun. I think I want to try a butt plug next. I am wondering if you have any recommendations for good plugs. Do you have a favorite? What should I look for when I buy one?

—Butt Plug Beginner

The traditional shape of a butt plug looks like a tear drop with a thicker bottom or a skinny pear shape. There are variations on the shape, including a lopsided diamond shape and a bulbous head with a long neck. Above the wide flared base, the plug’s neck has the smallest circumference, designed to allow the sphincter muscles to close around it. Butt plugs may be smooth or textured with ridges, ripples, rings, or bumps. Butt plugs are usually made of latex rubber or silicone; there are also clear acrylic (similar to Lucite), glass, wood, ceramic, and even metal plugs, but they are for more experienced anal players. Butt plugs come in a whole bunch of sizes, and remember that it is always best to start small and work your way up.

If you like the feeling of something just being in your ass, and appreciate the fullness and pressure without necessarily moving in and out, than you would probably love a butt plug. Butt plugs are meant to go in and stay in. Once you slowly slide a well-lubed plug inside the ass, you can then move on to something else — clitoral stimulation, a blow job, vaginal penetration, whatever you’d like — and the butt plug will continue to stimulate without a lot of work on your part. If you have a butt plug in, you may find that when you get really aroused or during orgasm, the plug inadvertently slips (or even shoots!) right out of your ass. While this may be surprising or embarrassing, don’t be alarmed, it’s pretty common. Remember that during arousal, your genital muscles contract, and those contractions may actually push a plug out of your ass. This doesn’t necessarily mean that the plug is too small and you need to run out and upgrade — it’s just a signal that you were very turned on!

Butt plugs are also a great way to warm up the ass for bigger things to come. Putting in a plug and leaving it in for a while lets the ass get used to having something inside it. The ass opens up and relaxes around it, and when you take it out, you’re ready to move on to something more.

Whatever kind of plug you select, it must have one important feature: a flared base. Perhaps you have heard rumors about people “losing” objects in their rectums and rushing to the emergency room. Or maybe you’ve seen one of several web sites which document X-rays of different items people have put in their rectums. While part of this is pure urban legend, the truth is you can get something lost in your ass if you aren’t careful. Once you are aroused, your pelvic muscles contract, and this could cause your ass to “suck” something all the way inside it. The best way to prevent your own trip to the ER is to use a toy with a flared base since the base will prevent it from going beyond the rectum and into the colon.

Double Penetration

Nov 052000
 


My boyfriend and I want to have a three-way experience—he and his best friend (a guy) and me. It has always been a fantasy of mine and he too wants to go through with it. We both swing, so we don’t mind seeing each other with another person. I have never really done this before. I have sucked another guy off while my boyfriend fucked me. However, I have never had two guys penetrate me at the same time, but I really want to do this. I think the idea of having two cocks in me—one in my pussy and one in my ass—would be an unbelievable feeling. However, this seems to be a hard thing to pull off. Do you have any tips on how to make this experience as pleasurable as possible?

—Fingercuffs

Congrats for being able to voice your fantasy out loud and tell your boyfriend. Fantasies can be incredible forces in our lives. When you share a fantasy with your partner, it can bring you closer together — and you can have a hot time in the process!

My first piece of advice is that maybe the two of you should practice some double penetration before you invite your friend over. Use a flexible vibrator or dildo in one of your holes and your boyfriend fills the other. Use lots and lots of lube, go slow, and work your way up to it. Communication is extremely important: you’re testing the limits of your body, so make sure you give your man plenty of feedback about how it feels.

Also realize that some women can easily and comfortably accommodate something of size in their pussy and in their ass. Others will take some effort, with lots of warm-up. But some women may not be able to do it at all, since double penetration really depends on your internal map, and if there’s room for two. You are the one who will know best if it’s possible, so make sure you’re the one who’s in charge and calling the shots. Work out the kinks on your dildo before you plan your threesome.

When you are ready to tackle two flesh cocks at once, use plenty of lube and go really slow. Depending on the size and height of all three of you, some positions will work better than others. You may want to straddle one man and have the other nail you from behind. Try to take one cock about halfway inside your pussy, then angle your body to take the other one in your ass. Both men should start with shallow penetration, so you can get used to the feeling. Remember that porn stars make it look easy in adult movies, but they are seasoned professionals! You may be much more awkward your first time around. Practice makes perfect.

Making it Fun for Her

Oct 192000
 


I love it when my wife wears a strap-on and gives it to me in the butt. My problem is that she only does it occasionally. I wish she would do it more and enjoy it more, but I think maybe it’s not to be. I’ve even thought about having a gay encounter so I can get fucked in the ass more. Any suggestions? Are there any women that like screwing guys?

—R.H.

Are there any women that like screwing guys? R.H., is the sky blue? Do I love getting fucked in the ass? Yes, yes, of course there are women who enjoy turning the tables and being on the other end of a nice butt fucking for a change. Unfortunately, your wife may not be one of these dildo-wielding divas. Since you’ve already gotten your ass plowed by her before, I think it’s fair to ask her directly why you’re not getting the backdoor gift from her more often. Have you told her how much it turns you on? Your wife may have some issues with being the penetrator (instead of the penetrated), since it is not a straight woman’s typical role; however, you can reassure her that there are plenty of other women giving it to their guys and loving every minute of it.

Perhaps she hasn’t realized her own potential for pleasure during strap-on sex. In addition to being a real turn-on upstairs (in her head), there are also plenty of ways for her to get off while she’s got her cock in your ass. For some women, when the base of the dildo rubs against the clitoris and vagina, there is enough friction there to feel fantastic. Your gal should also consider the power of having balls. Some women simply don’t choose a dildo with balls because they prefer a more non-realistic style dildo; however, balls do more than make it look real, they extend the base of the dildo and cover more surface area — which means more for you to rub up against. Think about it.

If she wants to add a vibrator to the equation, she has several options. She could select a vibrating dildo, which will deliver vibration to both of you. She could try to don a wearable vibrator beneath her harness, but this may be awkward and interfere with the harness being tight enough. A better idea is the Buzz Me harness made by Stormy Leather and equipped with a pocket for a small vibrating egg. Vixen Creations has several dildos, among them “Treasure Chest” and “Bobby Sue,” with hollowed-out bases. Stick a vibrating egg in the base of the dildo, tuck the battery pack in the side of the harness and she’s ready for vibrating action, his and hers style!

For double penetration (one for you, one for her), there are harnesses with two holes, one for the dildo to penetrate you with, another for a dildo pointing in her direction. The”Nexus by Vixen is not an extra long jelly dong like you see in adult novelty stores. Instead, it’s a two dildos-in-one package: she can have a dildo inside her pussy or ass while simultaneously penetrating your ass. I just love sex toy technology!

If you want to learn more about strap-on anal sex, I highly recommend the videos Bend Over Boyfriend 1 & 2.

Now, as for your idea about having a “gay experience” in order to fulfill your anal sex desires, don’t you think that switching teams might be a little too extreme? Unless you are actually bisexual, and looking for a way to express your desire for men, if it’s anal sex you want, I stay stick with your wife and see if both of you can get what you want and need out of the assfucking experience.

Cum Recipe

Oct 032000
 


I have a question about ejaculating dildos and butt plugs. I saw a “recipe” for cum that is made up of condensed milk, egg white and sugar. I want to use this in a ejaculating dildo. Is it safe to use this “cum” in my ass? Could this cause any medical problems?

—Jim

Well, Martha Stewart would certainly be proud that you are so enterprising! Ejaculating dildos and butt plugs are lots of fun; they give you the opportunity to experience shooting a hot load up your own ass or the rear of a friend. My first experience with a squirting dong came when I was sucking off a butch girl; she slammed her cock into my mouth, and at the same time squeezed her balls. Suddenly, a burst of fluid shot to the back of my throat, and the surprise alone made me soak the wood floor I was kneeling on!

I’ve heard that different people swear by different formulas for the perfect confection of fake jizz. The most important thing to keep in mind when getting out the measuring cups is that anything you put in your rectum will be automatically absorbed into your blood stream. A shot of sweet faux cum could leave you with a stomach ache. The one that you describe (made of condensed milk, egg white and sugar) creates an impressively life-like texture and aesthetic; if you were going for great visuals — a pop shot on someone’s mouth or tits, for example — that recipe would work well. If, however, your cum shot is meant to be an internal one, I would err on the side of caution and recommend that you simply use warm water. It will still feel quite real, and it is your safest choice healthwise.

Wanting to be Spread Wide

Aug 072000
 


I really enjoy anal stimulation and sex. It is the best way to have the best orgasm as far as I am concerned. I would like to know what I can do to be able to handle larger objects in my ass. An example would be a cucumber. I have such erotic fantasies about this and really want to move on to bigger things! I do not have a problem with a butt plug. The problem I have with trying bigger objects is that I orgasm too quickly. Just the thought of it makes me tingle. Any other advice you can give me?

—Wanting to be Spread Wide

So you’re a size queen, huh? Honey, I identify with you. I think it’s both noble and ambitious that you want to put bigger and bigger things in your ass.

My advice is pretty straight forward: work your way up slowly, don’t rush it, listen to your body. Use plenty of lube and have patience. If you’re using toys, make sure they have flared bases (you don’t want to lose anything in your ass) and are smooth. I find that butt plugs are a good way to warm up to larger toys because you can put one in and just leave it in for a little while. Your ass gets used to having something inside it, relaxes, and opens up around the plug. When you take it out, you’re ready for more. Some people like more of the in-and-out fucking with fingers or dildos, but that makes me sore more quickly than butt plugs (that’s just a personal preference though). Do what works for you.

As for the cucumber, well, I have two concerns. Most vegetables are sprayed with pesticides which are difficult to wash off completely; unless it’s organic, I wouldn’t put it in my ass. Some people have told me that cucumber peels contain a kind of natural substance which is irritating to the rectum and potentially dangerous; I suppose you could get an extra large condom for protection, but I say just stick to sex toys for safety.

The Perfect Butt Plug

Jun 102000
 

Do you recommend a good butt plug? I first used a cheap jelly one, but I am ready to upgrade.

Since I used to work at a sex toy store and I have tried such a wide variety of toys, I feel very qualified to recommend them to people. My favorite butt plugs are made of silicone instead of latex rubber. Although it is more expensive, silicone is worth it because of all its pluses: it’s easy to clean, warms with body heat, and will conduct vibration from top to bottom.

I am thrilled to share with you that I’ve found the perfect butt plug. Why is it perfect? Because I made it! I teamed up with Vixen Creations, one of the best silicone sex toy manufacturers, and helped design a butt plug with my namesake. I tried to incorporate all the pros of some of my favorite butt plugs and fix some of the problems with some of my least favorite models. The result is an awesome butt plug named for me, called simply “Tristan.” It’s not a plug for beginners, but those of you who already enjoy anal pleasure, I hope you’ll like this creation. You can buy my butt plug in my shop. Please let me know what you think!

Willing Anal Virgins

Apr 232000
 

My girlfriend said she is willing to have anal sex, but neither her nor I have done it before, and I was just wanting some start up tips. I hope you can help us because I am looking forward to doing it.

–Bob

Two willing anal virgins! Yippee! I am very glad you wrote, Bob, because I receive so many letters from backdoor beginners and first-timers seeking advice. You didn’t specify which of you will be doing the fucking, and who will be taking it up the ass; however, I’m going to assume that you want to fuck her in the ass. (The majority of men who contact me wanting to get fucked in the ass are usually pretty specific about it.)

I cannot stress enough that going slow and having patience from the start will really pay off for both of you in the end. One of the keys when trying something new is not to forget the tried and true techniques that are already working. Before you even go near her ass, get her revved up in the usual ways — her favorite oral technique, her favorite position, her favorite sex toy, etc. The more relaxed and turned on both of you are, the easier it will be. Make sure you have trimmed your nails (sharp edges suck!) and have plenty of water-based lubricant on hand — lube is an absolute must for anal penetration of any kind. Tease the outside of her ass with your fingers, your tongue, maybe a vibrator.

When she’s ready for you to penetrate her, use one well-lubed finger. Instead of going straight inside, touch the pad of your finger to her opening; this trick usually relaxes the anus, allowing you to slip your finger in. Don’t go too far too fast! Go up to the first knuckle and just stay there, letting her ass get used to having something inside. When she’s ready for more, slip farther inside her ass slowly and gently. Make sure that she’s the one in control of the action — and she should let you know if she wants more or less, slower or faster, deeper or not-so-deep.

You should set some realistic goals, because most women can’t go from zero to sixty in one session. Decide to work your way up to one finger, two, or a small butt plug on your first try; that way, you won’t rush things. Going too fast or trying to do too much is a surefire route to pain and discomfort, which we don’t want. Practice a few times with fingers or small toys before you whip your dick out. Repeat as necessary. When you’re both ready for you to put your cock in her ass, again work your way up to it, go slow, and let her guide the action. Use plenty of lube and have a blast!

Long-Term Plug Wear

Apr 172000
 

My boyfriend would like to insert a butt plug and have me wear it overnight. Is it safe to do so?

–Denise, New York, NY

I assume that you and your boyfriend are experienced anal players if he’s cooked up this little plan for you. I’d like to address your question and also talk about wearing butt plugs in general for readers who may be less experienced.

For many people, the feeling of fullness one gets from having a butt plug inserted is highly pleasurable, and some like to extend that pleasure for various lengths of time. My friend Susan wears a butt plug on long traveling excursions by car and train; she says it makes the time go faster. I know another woman who likes to wear a butt plug out on a date, in order to begin foreplay over dinner at a restaurant. Through each course of the meal, she is reminded of her ass, and with every shift in her seat, she prepares her ass for bigger things to come. I’ve also heard of plug lovers who like to wear a butt plug out in public just for the hell of it. These folks carry on everyday activities with a big smile on their faces. They like the feeling that they know something the rest of the world doesn’t. They are having a naughty sexual experience in public that no one else knows about but them!

Wearing a butt plug out in public or for an extended period of time can be hot, fun, and sexy, and here are a few tips to make it even better. First, you should work your way up slowly. Begin by wearing a butt plug for a half hour, see how it feels, how you like it, what works and what doesn’t. If your thirty minute excursion goes well, try an hour next time. Continue building up the amount of time (in reasonable increments) that you wear the plug. Like anything else you out in your ass, the butt plug should be well lubricated. You may want to consider taking it out every hour, re-lubing it and re-inserting it. Some of you purists may consider this cheating, but keep in mind that the lube will be absorbed by your body eventually, and the plug may get uncomfortable.

You have a number of options when it comes to making sure the plug stays securely in your ass and won’t fall out. You can purchase a butt plug harness which looks very similar to a dildo harness and does the job quite nicely. Sometimes a very tight pair of underwear, briefs, or a thong will keep it in, depending on the size of the plug and how strong those sphincter muscles are. My girlfriend loves to make a rope harness for me that runs between my legs. When I move, the rope rubs against both the plug in my ass and my pussy giving me a double sensation I just love. If you do use rope, make sure it’s not too tight and that it’s soft rope that doesn’t chafe or burn. Don’t make complicated knots that are not easy to remove in case you have to do it in a hurry.

Wearing a butt plug for a long time won’t block anything unless you need to have a bowel movement, and then (common sense) take it out, go to the bathroom, and you can put it back in.

Finally, on to your question about wearing a butt plug overnight. If you are very experienced with wearing butt plugs for long periods of time, I say, go for it. Make sure to use lots of lube, and you should probably take it out first thing in the morning when you wake up!

Wanted: Bigger Toys and Speculum

Aug 181999
 

My wife is 28 and I am 30; we have been married for three years. We are starting to get into anal sex. We have your book and want to experiment more — we even want to try fisting. Our problem is that we need more toys. The biggest plugs and dildos we can find are 2 1/4″ which feels like my max, but she thinks she can take more. Why is it that a big six foot man can only take a 2 1/4″ plug? Also, where can we get a speculum? Are there different ones for the ass and the vagina? How do you use it safely?

–Mr. G.

Wow, you’ve got a lot going on. I don’t know where you live, but I am assuming you’ve visited your local sex toy store and bought everything it’s sellin’. For more toys, I encourage you to check out two of the best sex toy purveyors in the world — Good Vibrations located in Berkeley and San Francisco  and Babeland in New York and Seattle. They both have an incredible selection of butt toys, from anal beads to high-quality silicone butt plugs and dildos by great manufacturers like Vixen Creations and Dils for Does. You may also want to check out some of the inflatable butt plugs and dildos on the market; you can go from slim to super with a few squeezes, making it a very versatile toy. As for the size issue, some of the lines of plugs and dongs marketed toward gay men seem to be of the size queen variety. Some of them are downright scary, even to Buttgirl.

So, it seems your wife can take a bigger plug than you, huh? Well, your height has little to do with how much you can stuff in your ass. My recommendation to you: practice, practice, practice.

As for your speculum request, you can find the disposable clear plastic kind and the metal re-usable type at medical supply stores (Babeland also carries them). Technically, a speculum is a speculum, and you should select a smallish one for anal use. If medical equipment and scenes are your fetish, you can also get some more expensive menacing-looking stainless steel speculums, and you can ask a medical supply house for an anal speculum. Make sure to use plenty of lubricant, insert the speculum slowly, and open it even slower.

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