This is a very common question — one that more than a few guys have struggled with. Niki Khanna, Education Department Manager at Good Vibrations, assures me that when she and other GV staff give pleasure parties (known colloquially, sometimes, as “fuckerware parties”), one of the most challenging things for many straight women to get their heads around is the idea of strapping it on for their men. But for many straight men, being anally receptive is a huge fantasy, whether as part of a larger role playing scene or just for the pure pleasure of it. How does one go about asking his girlfriend to try “wearing the pants” for a change? And what can the girl expect to get out of it?

You might be pleased to know that a large number of the harnesses GV sells are sold to hetero couples. If this is reassuring to you, you’re not alone. While strap-on play has only recently become a well-known phenomenon, many, many women have the fantasy of being sexually dominant, and strap-on play can be a great part of that. However, it’s not always about dominance and submission — women are often interested in anal play with men simply because it’s pleasurable to him. Many of the men I’ve been with have been very focused on their cocks, and had a hard time being receptive to all-body pleasure. Playing with a man’s butt is one of the most intense ways to break down that disparity.

To be honest, my experience is that many of the guys I know are more nervous about being penetrated anally than their girls are about penetrating them. Straight and bi women are often fascinated by strap-on play just because it’s something new and different — and I can testify from experience that it is definitely something different! Sometimes there is a stereotype that strap-on play is a “lesbian thing.” Sometimes it is and sometimes it isn’t — but it is also, quite clearly, a “straight thing.”

So how do get ready for your girl to strap it on for you?

Play with Yourself!

First, keep in mind that any anal play involves a lot of trust. For this reason, I highly recommend that you play with your butt yourself, if you haven’t done so. Dr. Jack Morin’s well-known Anal Pleasure and Health is the bible on anal play, but other popular books are Bill Brent’s The Ultimate Guide to Anal Sex for Men and Tristan Taormino’s The Ultimate Guide to Anal Sex for Women (since buttholes are, well, pretty similar between women and men). Some helpful videos are Bend Over Boyfriend and Bend Over Boyfriend 2 and Self Anal Massage for Men. Bend Over Boyfriend is more of a how-to video, while the second in the series focuses on erotic scenes of straight couples going at it. Both offer great inspiration for strap-on love. Self Anal Massage is primarily focused on gay men, but provides a lot of useful information, and many great relaxation techniques.

However, nothing says you need to get your advanced degree in sex before you experiment with anal pleasure. With a few basic pointers, you can find out all you need to know about your butt. The instructions in earlier articles in this series are aimed at women, but the pointers are all the same. To reiterate them briefly: The most important thing is to use lube. Not just some lube, lots of lube. A thick lube like Maximus, Slippery Stuff Gel or Astrogel is recommended because the sensitive tissues of the anus do better when they are cushioned by a heavier lube. A second important point is to try starting small — a finger sheathed in a latex glove or a smaller dildo like the Silk 1 is recommended. Latex gloves also smooth out those rough edges on your fingernails (a good manicure, by the way, is suggested), and the smoothness of the Silk often makes it easier for first-time players. There is plenty of time for you to try out the Johnny, Prince Sean Michaels Dildo, and if you’re a more experienced anal player perhaps you can skip right to that — but if you’re just starting out, remember that your eyes may be bigger than your butt.

Many people who enjoy anal play will enjoy a good rinse with warm water beforehand (your shower massager is your best friend here); not only does the gentle stimulation of warm water help relax you, but if you’ve got any concerns about cleanliness, that can help allay them. Enemas (also known as male douches) are also favored by some anal eroticists, but by no means necessary. If you’re going to rinse yourself out internally, be sure that you use a plain water enema; the Fleet enema that many drugstores sell is a good bet, but you should warm it up in a basin of warm water, first, because room-temperature water is quite a bit colder than your insides. A better suggestion is to use one of the refillable enema bulbs you can get in a drugstore (the ones I’ve used are blue rubber bulbs with white nozzles) and to fill it with warm tap water. If you’re exceedingly health-conscious you might be concerned about the contents of your local tap water — a reasonable concern, since the tissues of the rectum absorb anything in the water as efficiently as your stomach will. You may want to get a sink-mounted water filter, but make sure the water is warm. You can test it on your inner arm, just like you would for a baby, to make sure it’s not too hot.

Keep in mind that rinsing out your butt can dislodge material further up, so you may need to use more than one to get yourself good and clean. Fecal matter can sometimes be grainy or slightly abrasive, so irinsing out may make anal play easier.

I want to emphasize, however, that enemas are not in any way required before anal play — as long as you clean up afterwards and don’t get fecal matter in cuts or abrasions on your skin, anything you find up inside you is not going to hurt you or your partner. Latex gloves and condoms on your dildos will make cleanup easier, so feel free to forego the rinse if you’d rather. Enemas can also rinse away the beneficial (but scanty) mucus your body uses to protect your rectal lining, so keep in mind that if you’ve just rinsed, using enough lube is even more critical.

Lastly, you should avoid pain. That may sound obvious, but so many people expect anal sex to be accompanied by a little or a lot of pain that they often don’t stop when they feel it. If you lube yourself and the toy well enough and go very slow, you shouldn’t feel pain. If you do feel pain, you need to remember that pain is your body’s way of telling you to wait. If it hurts a little, you don’t need to stop necessarily — just slow down, take a break, and add more lube. But if it keeps hurting, or if it hurts a lot, you may have more going on than just a tight ass. Any of the books mentioned above helpfully describe the various anal maladies that have plagued erotic adventurers for all of human history; if you’re experiencing chronic anal pain, however, you should see your doctor.

Assuming you’ve experimented with anal sexuality on your own and want to incorporate it into partner play, how do you ask your girl to join you? I’m glad you asked! In the next installment of this series, I’ll cover ways to talk about anal play with your girl, and in future installments I’ll cover how to shop for a dildo and harness together, as well as some helpful hints for positions and other tricks that will enhance your erotic experience if and when you do feel her slide into you. ‘Til then!

We go out for dinner at a nice restaurant. I wear a sexy dress, but not too sexy, because it’s not the important thing. Neither are the pearl earrings, the make-up, or the way I wear my hair. What really drives you crazy are the heels, four-inch stilettos in red patent leather. I wear them without stockings, leaving my painted toenails exposed and my ankles circled by just the slimmest of shimmering straps.

You try to take your eyes off of them, but I won’t let you. We get a table in the corner so I can reach out with my foot and delicately tease your leg. You glance down at them and I can see the effect the high heels have on you. Your face reddens and you keep glancing down at them.

When no one’s looking, I slide my heels up the inside of your leg and nudge your cock. From the way you squirm, I can tell it’s already hard.

After dinner, we go walking in the park, and I take care to walk delicately, nudging my hip against yours to draw attention to the clicking of my heels on the sidewalk. Your breath is coming short. Your eyes go from my feet to my face and back again. They always rest longer on the feet.

We find a secluded bench, somewhere no one on the street can see us. There are other couples walking, enjoying the warm, romantic night. City people walk their dogs, barely giving us a second glance.

If I told you to, you would drop down on your knees and worship my feet right here. But instead, I curl myself onto far side of the bench, one foot under me, and put my other foot in your lap. Your cock surges against my feet as you begin to caress me. Your fingers trace the contours of the shoes gently, finding the places where the straps touch my bare skin. I’ve always had sensitive feet, and I shiver with every caress. Lucky it’s a warm night.

Every few minutes, I casually nudge my foot into your crotch, as if to reassure myself that you’re still hard. You are, and every gentle touch I give you makes you want me more. I can see it in your eyes. I can see it in the way you look from my feet to my face to my feet, trying hard not to let your hips grind against me too much. When people pass by us, I ease my foot out of your crotch and let my foot rest on your thigh as you stroke it. Just a poor working woman, tired from a long day, getting a foot massage from her devoted boyfriend.

By the time I take you home, you’re mad with desire. I tell you to make me a drink — it’s asking. really, but both of us know that tonight you wouldn’t dream of denying me anything — and I strip off my dress, sitting casually on the couch. I prop my feet up on the coffee table and look at you hungrily as you approach with my wine.

You don’t even have to say it. You hand me the wine, drop to your knees, and push the coffee table out of the way.

My feet are so sensitive that it tickles as your tongue embraces my toes. But every stroke of your tongue sends a surge of energy directly to my cunt, and as you get more and more excited, you tongue me more enthusiastically. The dress now gone, I’m wearing only panties and a bra. Normally I would have worn a garter belt and stockings for a dressed-up night like this, but I wanted my feet naked under the high heels. You lick your way up to my calves, worshipping first one leg, then the other. Your tongue caresses the ankle straps, then licks down across my feet and savors the place where the leather cups my toes. You lick your way to the underside and begin to caress the soles.

As you lick the soles of my shoes, I set my wine on the side table and my hand descends into my panties. I’m wet — gushing. My cunt throbs as I begin to rub my clit. I slip two fingers inside me and press against my G-spot. I return to my clit and rub in little circles as my excitement mounts. You move on to my other foot and hungrily devour that stiletto, too, taking a moment to lick up to my fleshy heel, pampered by today’s pedicure. The feel of your tongue on my bare flesh brings a shiver to my body. I rub my clit faster. Then I lift my foot, and you know what I want.

As you take the stiletto heel into your mouth, swallowing it as if it were a cock, I whimper. I want more.

“Take your cock out,” I tell you.

“Yes, Ma’am,” you answer, your mouth coming off of my stiletto heel for only the time it takes to say it. You unzip your pants, take your cock out, and begin to stroke it. I can tell from the way you’re breathing that you’re very close. But you won’t come until I tell you to.

I rub my clit faster, harder, feeling my orgasm approach. You hold my ankle delicately in your hand as I wriggle back and forth on the couch, my hips grinding involuntarily in time with your strokes as if I were fucking your face. Your mouth glides back and forth on the patent leather, your lips glistening with spittle. I cry out as I come, and in the middle of my breathy moans I tell you to do it.

“Come,” I order. “Come on my feet.”

Your mouth slides off of my shoe and you lean close to me, your cock pointed directly at my feet. I push them together so you can baptize them both at the same time. I see the effort on your face, your cheeks flushed with excitement. You let out a groan and your cock explodes, shooting come on my feet. The hot stream sends a pulse of energy through me, and you pump your cock until you’ve bathed my feet in your come.

You lick me clean as I sip my wine, smiling.

“Tomorrow we’ll go shopping,” I tell you. “I saw the most adorable set of pumps downtown.”

“Yes, Ma’am,” you tell me, and hungrily kiss my heel.

Still, there are many superlatives to strap-ons — especially with some of the fabulous recent developments in sex toy design.

Harnesses

Using a strap-on to fuck your man leaves your hands free to play with other arousal-inducing parts of his anatomy, and can give you a certain feeling of power that can be lots of fun for gender play or dominant-submissive exploration.

But first things first! Harnesses are body-fitting devices intended to hold a dildo with a broad base (flange) on a human body that’s not graced with an anatomical penis. When you select a harness, keep in mind fit, comfort and versatility for play. Some harnesses have “fixed rings,” meaning that the ring the dildo fits into cannot be changed to accommodate larger or smaller sized dildos. Also, harnesses fit differently depending on their features, and their particular style can affect your sex play. For instance, many of the harnesses we carry at Good Vibes are “two-strap” models, meaning they have two straps that hold the harness in place and run along the sides of your vulva, leaving you open and available for clitoral stimulation or penetration. Others will have little twists on versatility, but may have a single G-string-style strap or fit like a pair of shorts.

Some of our most popular harnesses are the Terra Firma, Thong Harness and Texas 2 Strap, but other harnesses may be more to your tastes. If your idea of a hot night in means a game of dress-up, you might want to consider something like the Vegas Harness or the fetishy Deluxe Rubber Harness. If you’re a larger woman, you may want to try the large-sized Vegas, Deluxe Rubber, Terra Firma or Texas 2 Strap, all of which fit up to 56-inch hips. As an alternative to the “straps” of the typical strap-on, the Spandex Harness (available in several sizes) is more like a tight bicycling short; many women find it more comfortable, since it has no straps to cinch or bind, but it can also provide less support because spandex stretches so much.

Some other great alternatives are the Easy Rider Harness and the budget-priced Mustang. Both of these feature elastic waists, which make them easier to take on and off quickly, and which some women find more comfortable since they don’t have to worry about buckles and tight leather straps. Again, since elastic stretches, these harnesses offer a little less support, but the convenience may be worth it.

If you’re interested in trying strap-on play but not sure what to buy, a good choice is the Strap-on Fever Kit, which features a Malibu Terra Firma harness, samples of Astroglide, Good Vibrations Condoms and latex gloves. It’s a good choice for your first explorations, since it includes everything you need to strap it on.

Lastly, there’s one of my very favorite toys, the Thigh One On. This simple but ingenious toy straps around your thigh and fits a dildo, giving you the extra thrusting power of those awesome quadriceps you built up on that damn stair-stepper. It may not sound like much, but believe me, the thigh muscles are much stronger than the back muscles, and as great as thrusting feels with a conventional harness, you’d be amazed what that extra oomph can bring. A pair of partners (of any gender) can each wear one for simultaneous penetration. What’s more, it’s machine washable and totally affordable! I can’t say enough good things about this dandy little toy.

You might also want to pick up the Driver Pad, a pad that’s the perfect shape to cushion your pubic bone. Prolonged or vigorous thrusting with a harness can give you bruises, and this accessory can help prevent that.

Dildos

Next, you’ll want to select a dildo to go in your harness (unless you bought the kit). While the price can be an issue, silicone is much, much more versatile and durable than jelly rubber. My favorite harness-compatible dildos are the non-representational Silk 1 and Silk 2, because a whole set lets you experiment and slowly move up in size if your man likes that. They’re totally smooth, which makes them great for nervous beginners because it means there are no rough edges, bulbous heads or veins to complicate things. Simple and straightforward, these dildos are a good, safe choice.

There are plenty of other great choices, though. When picking a dildo to fit in your harness, keep a few things in mind: Do you (or your partner) want it to look like a penis? Popular realistic or semi-realistic harness-compatible dildos are the Leo, Rex, Adam, Little Pal and Champ. All of these are silicone and representational, which can often add a lot to your fantasy play. Dildos with realistic “balls,” which will work in a strap-on but may not sit as smoothly, are Johnny and Riley. Keep in mind that you need a dildo with a flange, or a wide part at the base, or it won’t stay in the harness.

If you or your guy would rather not have a dildo that looks like a penis, try the Queenie, Jane Doe, Wave Pink Glitter, Babe,Willow or Corkscrew. The Hot Rod and Bobbi Sue fall somewhere in between, with a vaguely penis-like shape but less realistic than some others. If you’d like to add vibration to the mix, the Cosmo or Buzz are both harness-compatible dildos that fit a tiny vibe in the base.

Technique

A few pointers once you’ve got your gear selected: You can put the dildo in the harness either before or after you put it on, but if you’ve got a buckling harness it’ll be easier to put on before you tighten the straps. Depending on how the harness fits, you may find yourself with a serious downward-pointing cock or one that’s a bit more perky. Either way, a strap-on is definitely not a penis, so don’t expect to be able to use the same positions or angles your boy might use if he was on the giving, rather than the receiving, end of penetration.

This is where experiment comes into play. Check the previous articles in this series for suggestions on which positions work best for male penetration. Keep in mind that you can never have too much lube, and you should put lube both on the dildo and on your boy’s butt. Some good anal lubes include Maximus, Wet Platinum, Astrogel and Slippery Stuff Gel. These thicker lubes are often preferred because the rectum absorbs water very quickly, and a thicker lube lasts longer — as well as offering more cushion.

Again, it’s a good idea to start with a glove-sheathed hand, and work up to the dildo once your boy lets you know how good it feels. Go slow, and if you’re using a dildo with a wide head, keep in mind that the head is the slowest part to go inside. Once the head is inside him, give him a moment to adjust — and then, if he’s willing, enter him slowly with the rest of the shaft.

Don’t forget that you’ve still got two hands! Whether you use them to guide his hips back against you, push his butt onto your cock or reach between his legs and stroke him, your hands are instruments of great pleasure. What’s more, you can use them to touch yourself, playing with your breasts or working a hand into the harness to rub your clit. There’s nothing wrong with enjoying yourself when you’re giving him pleasure! In fact, if you’re like me, you just may find that strapping it on is one of the greatest pleasures you can have.

Good luck, and happy exploring!

With the help of the GV mail order staff, I narrowed down the overwhelming selection to a few prime candidates. I decided to stick with silicone, since it’s always been my material of choice. I also narrowed it down to realistic or “representational” dildos, which are made to look (more or less) like male anatomy. Finally, since I’ve always liked a little texture with my toys, I picked the Throb, Johnny and Mister dildos — and since I thought I might want to experiment with something a little bigger, I also picked up the Randy. I thought maybe my eyes were bigger than my, um, appetite, but I definitely wanted to give the larger toys a try. For me, with dildos size does matter — but bigger is not always better!

I settled back with an assortment of my favorite lubes: Liquid Silk, Maximus and Astroglide, and prepared for an evening of test driving.

After a good long warm-up with my favorite new erotic video (Mondo Porno), I took a moment to get to know my new best friend, the Throb. At 5 1/2″ long and 1 1/4″ in diameter, it’s a nice smallish dildo that fit my tastes perfectly. As I slid its lubricated length into me, I noted that its crisscross of veins definitely added sensation. It also had an almost springy tightness or hardness to it, which made it perfect for adding pressure up against my G-spot. It’s also shaped with a little upward curve, which adds to the G-spot stimulation. I noted with pleasure that its flared base also meant that the Throb would fit nicely into my strap-on, so my partner could enjoy what I was enjoying. Soon I was having a grand old time, but I had promised myself I’d try all my new toys in one sitting. I used that clever “A to B” feature on my DVD player and watched a repeating segment of one of my favorite scenes while I eased out the Throb and moved on to Mister.

Mister is exactly the same dimensions as Throb, but felt quite different. The main difference here was a less rounded head and less prominent veins. Something about the way Mister is shaped made G-spot stimulation less satisfying — as did the fact that it felt slightly more pliable than Throb, lessening the firmness of the sensation. I enjoyed it quite a bit, but decided if I had to pick between them, I’d be happier with the Throb — purely based on shape. Feeling both deeply satisfied and deeply needy, I moved on to Johnny.

Johnny is a bit thicker than Throb or Mister — at 1 7/8″ in diameter — but feels a whole lot bigger, perhaps because of the extra 1 1/2″ it adds in length. Something about the shape of its head also made it seem larger as I eased it into me. I have to admit, its ultra-realistic shape (complete with sculpted balls!) was a turn-on to me, and its subtler veins also added sensation while being easier to move in and out. I also liked the extra length — while I didn’t really need the extra 1 1/2″ to fill me up happily, it was nice to have the extra handhold. It had the same gentle curve as the Throb, which allowed me to nestle it firmly against my G-spot, and the texture and hardness of the two dildos were roughly equivalent. I realized I was behaving in classic size-queen fashion — I’d started small and moved up to slightly larger toys. Now, the one dildo I had left to try out was the Randy.

Ah, yes, the Randy, that dildo that had sent such a quiver through me when I’d first looked at it. At 2 1/4″ in diameter, it’s quite a hefty companion, and I was looking forward to seeing if it was too much for me. It took quite a bit of lube and a little patience to get it snugly pressed inside me, but I have to admit, that girth did get my attention. However, much as I enjoyed the feeling of thickness, the tightness it created made it a bit more difficult for me to move the dildo (even with a lot of lube) and to get the G-spot stimulation I was craving. Much as I liked Randy (and I’ll admit, its size remains a turn-on to me), I found myself returning to my friend Johnny to finish the evening of merriment.

I came away from this rapturous research having learned one very important thing — it’s hard to predict what dildo is going to satisfy you. While size and shape can be a good indicator of where to spend your money, what I discovered is that the subtleties of shape make it advantageous to try out a variety of toys to see which ones work with your particular anatomy. While I definitely enjoyed all four dildos I tried out, I found that something about the shape and firmness of both Throb and Johnny really fit the bill. I look forward to trying out more toys — but for now, I’m thrilled to have found two that work so well for me!

And anyone who’s read my previous articles in “Male Sexual Pleasure” knows that I’m not shy when it comes to using sex toys with guys. After all, men can enjoy vibration as much as women can, and there’s nothing that says women have the market cornered on enjoying penetration. But it’s always seemed to me that sex toys designed for the pleasure of the male anatomy — that is to say, cock and balls — were a little in short supply. I admit it, no man I met would ever admit to trying those “pocket pussy” things that you see in the less fashionable boutiques, and let’s not even talk about blow-up dolls.

But I’ve noticed that recently the innovative philanthropists in the sex toy industry have come up with a greater variety of toys specifically designed for pleasuring the penis. Far from being odd testimonies to porn weirdness, these toys are tasteful and carefully designed. With the help of my male assistant, I decided to try them out. I have to admit, from the results of my decidedly non-clinical trial, I wish I had a cock. Then again, it’s not the first time.

My partner’s name was Shawn, a fetching and slightly younger man who I’ve been friends with for some time, with more than occasional flirting. It seemed like a good way to break the ice, don’t you think? He warmly agreed to be my test subject, though I didn’t tell him what he would be testing. I love surprising men with toys.

Next came the toys themselves. While Shawn had volunteered to come to Good Vibrations with me to pick out the toys, I loved the idea of laying these toys out on the bed for Shawn’s discovery. I went to the Valencia Street store and explored the options for sleeves. I wanted to make sure this was a complete trial, after all!

The Fleshlight, Ecsta-Sleeve, and Main Squeeze all come in “anus” and “vulva” styles. The Fleshlight also comes in plain. I’ll admit, the selection boggled my mind. I had no idea what Shawn would prefer — and my attempts to suss out whether he would prefer pussy or ass based on our flirting sessions proved utterly fruitless.

One of the helpful staff members suggested that while the sensations between the vulva and anus versions of the same sleeve would be pretty much the same, for many men the choice is about fantasy play. Excited that I was getting to know Shawn, I decided to buy one of each. No point in being shy! I also got bottles of my two favorite lubes, Slippery Stuff and Liquid Silk.

Shawn came over for dinner and a glass of wine with full knowledge that we were going to spend the evening in the pursuit of male sexual pleasure with the help of the mysterious sex toys. During dinner, I kept teasing him, refusing to tell him what it was he’d be testing. I could see him blushing and getting a little turned on whenever I mentioned it.

After dinner we sat on the couch and started kissing, enjoying the feel of getting to know each others’ bodies when we’d been friends for so long. We were good and ready for the pursuit of pleasure, and after a long, slow make-out session, I took Shawn by the hand and led him down the hall.

His jaw just about dropped when I opened the door to my bedroom. All six toys — anus and vulva versions of the Fleshlight, Ecsta-Sleeve, and Main Squeeze — were on big fluffy towels on my king-sized bed. I’d rinsed them all out with water and let them dry, and now they blessed my bed like a sexy buffet. Shawn started to giggle.

“Is this okay?” I asked him, gesturing toward the bed with its array of pussies and anuses.

“This is so okay,” said Shawn, his face flushed red and his cock standing at attention, distending his pants invitingly.

We slowly undressed each other and moved the toys over to one side of the bed. I caressed Shawn’s cock as I kissed him, making sure that he was good and hard. Then I asked him if he wanted to choose which toy to try first or if I could. He said he wanted me to choose. Smiling, I picked up the vulva Fleshlight and showed it to him. His eyes widened and his breathing quickened. I drizzled a few drops of lube into the opening and smeared some more over the head of Shawn’s cock. The flashlight-shaped case was what gave the Fleshlight its name, and it provided a helpful handle. I teased Shawn, sliding the head of his cock between the fleshy lips of the toy, and then, holding the base of his cock with one hand, I used my other to push the toy down onto his cock.

My pussy gave an involuntary twitch as the Fleshlight enveloped Shawn. Jealous? Not really. But I had to admit, the vulva shape was working for me.

“What does it feel like?” I asked.

“Wow,” he said. “It’s got ridges.”

“Does it feel like a pussy?”

“Kind of,” he said. “It feels great.”

I smiled and kissed him. Shawn began to moan as I slid the Fleshlight up and down on his cock. Seized with a wicked idea, I told him to get up on his hands and knees, and then I positioned myself under him, holding the Fleshlight.

“Fuck it,” I told him, and his hips began to slide back and forth.

Soon Shawn was moaning, and he warned me that he was likely to come soon. I asked him if he wanted to come and he said he’d like to play more before he did, which made me grin. Knowing that we had lots more toys to choose from, I rolled him onto his back, slid the vulva Fleshlight off Shawn’s cock and replaced it with the anus Fleshlight after refreshing the lube. Wanting to “enhance his fantasy play,” I showed Shawn the puckered opening of the “anus” first, and smiled. As it slid down over his cock, Shawn gasped.

“Is it different?”

“I don’t know,” he said. “It seems tighter.”

“They said it wasn’t,” I told him. “Maybe they lied?”

“Or maybe it’s just my imagination,” he said, and then he wasn’t saying anything. I was sliding the Fleshlight up and down on his cock.

“I like that one,” he said.

“Better than the pussy?”

“Wow,” he said. “That’s like asking if I like Rocky Road or Dulce de Leche ice cream.”

I playfully spanked Shawn’s thigh and told him if he was going to be sarcastic, he could just say goodbye to the Fleshlight. He made a disappointed noise as I slid it off his cock, but as I replaced the Fleshlight with the Ecsta-sleeve, his smile returned.

The Ecsta-sleeve didn’t have the case that the Fleshlight did. Rather, it was just a gooshy sleeve in my hand — probably why it costs less than half as much as the Fleshlight. It took a little getting used to, since it was slightly harder to keep hold of. But soon Shawn was moaning just as loudly as before. I had been so excited about trying the new toy that I hadn’t even checked which one I was grabbing — it was the anus (curiously enough in boy-blue, as opposed to the vulva Ecsta-sleeve, which is girly-lavender).

The softness of the Ecsta-sleeve allowed me to control how tightly I gripped it, and to feel the swell of Shawn’s cock inside. That was an unexpected pleasure to me, and soon I was having lots of fun controlling how I held the Ecsta-sleeve to change the sensations as I stimulated Shawn’s cock. I got more and more turned on myself as I explored the different angles I could use the sleeve — once I had the hang of it, the Ecsta-sleeve actually offered more versatility than the Fleshlight, though I’ll admit it was nice to have the case to hold on to.

I pressed my body against him as Shawn mounted toward orgasm. I kept pumping the blue Ecsta-sleeve onto him as his hips lifted off the bed. “But we still have toys to try,” he whimpered helplessly as I stroked him off — and then he came, clutching me close, his whole body shuddering as our long session of teasing and testing paid off with what was clearly a mind-blowing orgasm.

We never did get to try the Main Squeezes or the vulva Ecsta-sleeve. After we’d cuddled for a while, things progressed into exploring different avenues of orgasm (i.e., mine) and while Shawn and I spent most of the night getting to know each other, we never made it back to the toys that night.

Cleanup was much easier than I expected — I held the Ecsta-sleeve open under running water and before long it was squeaky clean on the outside. You can also use mild soap with it, but I didn’t find it necessary.

After trying both the Fleshlight and the Ecsta-sleeve, I would compare them thusly: The Fleshlight is easier to handle and a little easier to store. The less expensive Ecsta-sleeve actually offers the unexpected benefit that it’s more flexible and therefore gives you, the handjob-giver, more sensation as you use it. The Fleshlight, however, can be adapted for use in that way — its insert slides out of the plastic case, though I didn’t find it quite as easy to handle as the Ecsta-sleeve. Still, that is a great option, and the Fleshlight case can be used strictly for storage if you prefer to use the insert alone.

I’ll admit that I’ve gotten over any reticence I had about the idea of men’s toys. On the contrary, I’m very much looking forward to making men’s sleeves a part of my routine with Shawn. And something tells me they’ll always have a little sentimental value for us, too!

It wouldn’t have tempted me so much if I wasn’t dressed up like a damsel in distress. White fluffy dress, cut very close and showing a lot of cleavage, drawing stares from everyone at the party, women and men alike. Not to mention the dual slits up my legs, so high that they almost reached my hips. My blonde hair was in pigtails, my eyes painted so they looked even bigger than they are — big and bright and utterly without guile. Very sexy, but virginal.

I mean, the whole innocence gone wrong thing really appealed to me, and it was kind of turning me on knowing I looked sexy enough to draw stares from everyone. Usually Halloween is when people break out their sexy personas, the schoolgirls and sluts and cheerleaders and vamps and French maids they always wish they could be. Not this crowd.

There weren’t even that many costumes — maybe half of the guests were dressed up, and those ones had gone for… you know, the usual lame costumes selected by people without much time to create. Lawyer types dressed as James Bond. Computer-geek army men. One woman dressed like a judge, waxing philosophic on the importance of having women on the Supreme Court.

It’s not like we planned it that way, but when a party gets boring enough, you need something to keep you occupied. And Jake’s always good at keeping me occupied.

Jake? He’s into costumes. He found me the dress, even bought it for me. So maybe it was his idea to begin with. His costume was better than mine. He’d gone for the face paint and even a bit of a rubber prosthesis — a big gash in his head, running from his pallid chin to his pallid forehead, oozing what looked like blood. Really, really gross. It was Halloween, after all.

Jake’s a big guy, 6′6″, more than a foot taller than me with broad shoulders and muscles. He doesn’t even work out and he stays in perfect shape, his chest developed and his belly and legs slim and sinewy. I hate him for that. But then again, I love him for that.

“Ugh,” Jake grunted at me, leaning over and nuzzling my ear as we sat on the couch listening to some loser spin another tale of dot-com riches gone poof.

I swatted his arm. “Don’t get friendly,” I whispered. “If you think I’m going to make it with a zombie, you’re dead wrong, mister.”

“Dead,” he grunted into my ear. Then, quieter, “Zombies have supernatural strength,” he said. “You’d be helpless to resist.”

I elbowed his hard-muscled six-pack abs and put my lips to his ear. I whispered: “Just try it, Maggot Man. We’ll see who’s helpless to resist.”

“Zombies need love, too,” he whispered.

“Some zombies need a spanking.”

“That, too,” I heard him say.

“What are you two whispering about?” sighed Annette, one of the hosts, as she breezed by the sofa picking up discarded plastic cups. She was dressed as a fairy princess, her high-peaked cap smacking the chandelier and falling off every time she passed under it. “Care to share it with the rest of the class?”

“We were just discussing zombie love,” said Jake.

“I hear it’s quite compelling,” winked Annette, and flitted away.

“What’s with her?” I wondered in a whisper.

“She said we could use their bedroom,” Jake said softly.

“For what?”

“I told her you had a headache,” he whispered. “I said you might want to lie down.”

“I don’t have a headache,” I hissed.

“I’ll give you one,” Jake said.

“You are already.”

“Good,” he said, and got up from the couch. Grasping my hand, he all but dragged me with him.

“Excuse me,” he said to the other guests clustered around the couch. “I’ve got to go fix my makeup.”

“Jake,” I protested as he dragged me along the hallway. “This is rude.”

“It’s a scientific fact that zombies have no social skills,” he said, pushing me toward the staircase. “But they have enormous sex drives.”

I felt a quiver go through me as he said that; was he really being that blatant? He was telling me that he was going to take me upstairs and fuck me in his zombie costume?

I looked at him, admiring the weirdness he’d poured into his costume: the caked blood on the tattered suit coat, the big gash in his head. But more than that, I admired the way the black, threadbare suit matched the contours of his body.

I turned and hurried up the stairs.

I had never been in Annette and Mike’s bedroom; they were friends of Jake’s, not mine. It smelled unfamiliar, a mix of potpourri and incense with the hint of strange bodies underneath — unique, the way every lover’s bedroom smells different the first walk into it. They had framed prints of Klimt on the walls and a smattering of candles around the bed. The candles had been lit. More importantly, they had a big king-sized bed with an enormous, heavy wooden frame. At the head of the frame, they’d Velcro’ed three different kinds of lube in big pump bottles.

And right there in each corner, metal restraints were bolted directly to the frame.

Jake closed the door and locked it.

I turned, my eyes wide. “Wait a minute,” I said. “I didn’t know Annette and Mike were kinky!”

“Very much so,” he said. “Even kinkier than us.”

“You’re not thinking…”

“Zombies have inordinate strength,” he said, and grabbed me.

I felt like I should argue with him, but I just sort of melted into him. When Jake and I make love I adore the feeling of his huge bulk on top of me, his strong arms crushing me to him. I love the feeling of losing myself in his hugeness. The only problem is that he really does have an enormous schwanzstucker. And as for me, I’m not exactly built like the Bride of Frankenstein, know what I mean? Jake’s the most patient, understanding, gentle lover I’ve ever had, though, so it’s all good.

But this was a zombie, right? A monster. He’s supposed to have an enormous one, in any event.

More importantly, there was something hot about Jake’s costume. Dangerous. Scary. Don’t they say fear is an aphrodisiac?

“What if Mike and Annette walk in?” I asked as Jake began to untie the back of my innocent-virgin dress.

“They won’t,” Jake said. “I told them I was bringing you up here to fuck you.”

“Um, excuse me? Come again?”

“They’re cool,” he said as he pulled the last fastener and my dress slipped off my shoulders, pooling around my feet. I stood there in a white thong and no bra, white four-inch heels on my feet lifting my head to only a foot lower than Jake’s.

I could feel my nipples hardening against the wool of his thrift-store suit.

“On the bed, prisoner of love,” he told me.

“Or what?”

Jake and I like to play games a little, and that was all the opening he needed. He seized me, his hands firmly gripping my shoulders, and pushed me back onto the bed. I gasped as I went bouncing onto it. Under Jake’s bulk, I was helpless as he fitted my wrists into the cool metal restraints and clicked them closed.

“I hope you have the key,” I whispered.

“Nope,” the zombie said cheerfully. “Annette has it.”

“What?” I hissed, pulling against the restraints — but by that time, Jake was down at my legs, forcing my ankles into the manacles.

He had to stretch my legs wide, very wide, to get them to fit.

“I think the bed’s too big,” I squeaked. “Can you loosen them at all?

“Annette’s taller than you,” said Zombie Jake. “That’s as loose as they get.”

I lay there, utterly immobilized, stretched out on a stranger’s bed, manacled. I was stretched so tight I couldn’t move even a little bit. I was spread wide, my pussy exposed except for the thin slip of fabric that made up my thong.

Jake stood next to the bed and surveyed his conquest: me, spread-eagled in an X of surrender, slim breasts peaked with hard nipples as it sank in that my boyfriend was going to fuck me like this. I was about to be taken.

I was still in the innocent-virgin mode, and discovering it was a huge turn-on for me.

“Please,” I whispered breathlessly. “Be gentle.”

“Zombies never gentle,” he grunted. “Zombie love is hard love. Zombies eat human flesh.” He made a dramatic face, which got me giggling a little.

Jake shrugged off his blood-spattered suit coat and pulled his T-shirt over his head, careful not to disrupt his head wound. He quickly undid his pants and let them fall, then stripped off his boxers and kicked off his shoes.

Standing there nude except for face paint, a prosthetic head wound, zombie face makeup with whiteface and trickles of blood running out of his mouth — I have to admit it, but Jake looked strangely compelling.

More compelling, though, was his hard cock, standing full and hard and huge, with its gentle curve beckoning to me.

Whenever I see it hard, I have to admit my mouth just starts watering. I squirmed against the steel manacles, feeling helpless, wholly owned. I could feel my pussy getting wet as my eyes ran up and down Jake’s hard cock. I could feel my throat aching for it, could feel a thin dribble of saliva forming at the edge of my mouth. I slurped, perhaps a little louder than I needed to, and licked my lips.

Jake could see me looking at it. He knew what I wanted.

“Zombie need virgin,” he grunted. “Evil jungle zombie god need virgin sacrifice.”

“Cut the zombie crap,” I breathed, “and come over here and put that thing in my mouth.”

Zombie Jake crawled onto the bed, holding me down with his bulk as he squeezed his knees and his folded legs awkwardly into the space between the top of my head and the headboard. I opened wide and he guided his cock to my mouth, sliding it in until the head reached the back of my throat.

It tasted divine. I wanted to moan, but my mouth was so full. I ran my tongue along the underside and swirled it over the head, tasting his pre-come. I felt my pussy throbbing, hot and dripping, as I pressed my face up against him, coaxing him to press deeper into me.

It was a good position for doing it. Deep throating, I mean. Some girls aren’t into that, I know. But nothing turns me on more. I’ve been working on it ever since I started going out with Jake. All I have to do is take a deep breath, hold my neck straight and swallow.

And I swallowed Jake smoothly, filling my throat as he slid into me.

I was so lost in the taste of Jake’s cock and the feel of it sliding down my throat that, even though I heard him grunt “Zombie must eat human flesh,” it didn’t register until I felt him pulling my thong aside.

By then, his tongue was so close to my pussy that there wasn’t even any time to anticipate it. It slid hard against my flesh, and he knew then — if he’d had any doubt — just how wet I was.

I laid back, neck straight, and felt Jake slowly grinding on top of me as he slid his cock down my throat. It’s a more complicated sort of motion than one might think, but my favorite zombie has gotten very coordinated. So much so that he was able to fuck me slowly, smoothly, sensuously while his tongue found my clit.

If I hadn’t been so full, I would have gasped; I would have moaned. As it was, I couldn’t make a sound, not even low in my throat, as I felt the tip of his tongue starting to work my throbbing, swollen clitoris. I felt my body straining instinctively, trying to arch my back, lift my ass off the bed, press my pussy more firmly into his face. But I couldn’t; locked in Annette’s restraints, I was stretched to the limit. All I could do was lay there and let Jake use my mouth as he licked me, mercilessly, knowing exactly the touch that would make me explode into the stratosphere.

I wanted to say it. I wanted to moan it. I wanted to tell him, “Jake, baby, I’m going to come,” but I couldn’t. All I could do was lay there. All I could do was lay there, dissolve into the sensation of his tongue on my clit and let him slide down my throat, pulling back every few seconds to let me breathe before sliding in again.

But he knew it was approaching. He could read my body, could tell from the way I tensed and struggled against the bonds that I was getting very, very close.

Which is good, because he slid his cock out of my mouth, leaving me panting and drooling, spittle covering my face and running down my chin, my mouth wide open as I finally let the wrenching moans explode from my mouth, let him know that I was only seconds away.

When I came, I tried to buck, tried to fuck my pussy against his face. It was my body, moving, like a zombie’s, no brain to tell it to stop.

But it didn’t matter. It was hopeless, because I was stretched so tight I couldn’t move. All I could do was pull on the chains, moaning and whimpering and coming as Jake’s tongue drove my clit over the edge.

When my moans quieted, I gave Jake’s cock one last, savory lick, running my lips up and down its enormous length. Then he pulled away and crawled on top of me.

Between my legs.

I knew what was coming, and I felt that momentary pang of vague fear and intense, overwhelming arousal that comes from knowing that Jake is going to enter me. I didn’t even realize it until I felt him guiding his thick cockhead to my pussy, though. Didn’t realize that he’d reached up to the headboard and squeezed a thick glob of lube into his hand, smeared it over his cockhead, slicked more of it around the entrance to my pussy.

Usually we use lube when he fucks me — lots of it – but I guess it still caught me off guard. I was still wrapped in the costume of an innocent virgin, naive, about to be taken by a huge, scary monster — even though the costume itself, all but the thong, lay in a limpid pool at the foot of the bed.

“Zombie god demand virgin sacrifice,” growled Jake, and entered me in one smooth, hard, well-lubricated thrust.

I was so wet, so turned on, so opened, that it went into me easily; his cock took me in a single rapturous push, possessing every inch of my cunt as his big zombie body settled on top of me. I always get a little tighter right after I come, but everything feels so much better — so even the taut embrace of my pussy around Jake’s huge cock made me moan with delight. I would have pushed up against him, would have lifted my ass to meet his thrust — but I couldn’t move. I was his prisoner.

Jake began fucking me as I looked up into his zombie eyes. The prosthetic head wound was beginning to melt, and his face glistened with sweat, making the makeup run. Coagulated stage blood went liquid again and dripped down onto my face. The gash was disintegrating, pulling free from his flesh and turning into a mass of goo as he fucked me harder.

He looked ridiculous. I didn’t laugh, though, because all I could say was, “Fuck me, zombie master. Make me your zombie princess.”

Jake ground his hips slowly, leaning heavily so that his pubic bone pressed against my clit. I gasped as he did that — he knows it’s the perfect way to make me come.

“Fuck,” I moaned. “Fuck, yes…”

I was going to do it again, maybe before he did. I wished I could grind against him, wish I could push up and help him take me, help him fuck me, help him make me come. But I was immobile, and as I dissolved into the sensation of being fucked helpless, I felt my orgasm building, utterly out of my control — and then I came, stretching my limbs against the manacles, my breath choking in my throat as I closed my eyes as tight as I could. My climax exploded through me.

An instant later, my zombie lover grunted, this time not a stage grunt but a real one, an uncontrolled rumble of pleasure followed by a monster howl as he came inside me. The sensations of my pussy contracting around his thickness mingled with the feeling of slickness as he filled me with his come.

Still moaning, bathed in afterglow, I opened my eyes.

Jake’s head wound finally dislodged from his head and went glop on the pillow next to me in a wet red mass.

“Oh, fuck,” he sighed.

“See?” I giggled. “It’s true what they say. Love heals all wounds.”

“I don’t think Annette and Mike are going to see it that way,” he said, eyeing the stage-blood stain he’d made on their pillow.

“Tell you what,” I whispered. “I’ll convince them.”

First, let’s be sure of what we’re talking about. In its most commonly referred-to form, double penetration is the simultaneous penetration of a woman vaginally and anally. What the porn industry calls “DP” means there are two men involved — that both of the phallic instruments are real, live cocks. While that can be a delicious fantasy, it’s somewhat less common for most women to try it in private life, if only because most of us don’t have threesomes with two men on a regular basis. But there’s much more to “DP” than just a single sex act.

For example, another kind of double penetration is vaginal or anal penetration mixed with oral sex (simultaneous oral with vaginal/anal penetration). And men can enjoy receiving double penetration as well, don’t forget, enjoying anal and oral receptivity at the same time. Since simultaneous vaginal/anal penetration is the most common act thought of when the term “double penetration” is used, that’s what I’ll be talking about here.

While the “gold standard” in porn may be two men on one woman, sex toys give us a world of possibility for enjoying this much-fantasized act, whether we’ve got male partners or female partners, two partners, one, or we’re enjoying ourselves alone.

Double Penetration with Sex Toys

First, the basics: if you’re going to involve your butt, we recommend reading our Ten Rules of Anal Sex and our Exploring Anal Sex Handy Shopping Guide. The simplest rules, however, are the most important: go slow, stop if you feel pain and use lots of lube.

Second: be sure that nothing that goes in your butt then goes directly in your vagina, since infection can result. Since latex or jelly rubber toys can’t be sterilized, if you’re going to use a toy in your anus that you might later use in your vagina, simply cover it with a condom. Silicone toys can be sterilized, so after you use one in your anus you can use it in your vagina as long as you boil it first. See our Toy Care and Cleaning Guide for more information.

Some companies sell toys specifically designed for simultaneous vaginal/anal penetration. These usually take the form of two joined dildos with a handle. These aren’t actually ideal for double penetration play, for two reasons: size and angle. It’s likely that you have different preferences as far as size and shape goes when it comes to your vagina and or anus. Buying one double-shafted toy means you won’t be able to select just the right tool for the job; one side or the other is likely to be too big or too small. And when it comes to angle, keep in mind that neither the vagina or the anus points straight back; they’re both curved, and the curves vary from woman to woman. Keep in mind that toys like our popular Nexus and Nexus Junior are excellent for two partners to share, but not really designed for a single person to enjoy. The Double Daisy can be adapted for that purpose (by bending it over — with a little muscle), but most people don’t find it ideal.

Your best bet, then, if you’re interested in playing with double penetration, is to select two different dildos or plugs. When selecting your toys, keep in mind that the vagina and anus occupy fairly close quarters, so if you select, say, the Sean Michaels Dildo and the Prince, things are going to get a little snug. That may be exactly what you want, but if you’re just getting started in double penetration, you’re likely to be satisfied with something smaller than you’re used to in both places. Also, with both anus and vagina feeling full (and a fairly small amount of tissue between them), veins or ridges may feel much more prominent than they would otherwise. Therefore, a smooth toy may feel better. Excellent choices for dildos are the deliciously smooth Silk toys, which have a variety of sizes and can be sterilized because they’re silicone. Also, since they can be sterilized, if you buy one size of Silk and discover that you’d prefer that size in your anus rather than your vagina — or vice-versa — you can sterilize it and switch! Other smooth dildos include the Bobbi Sue, Buzz, Treasure Chest and Champ. Each of these models has a flared base, which means that it can be safely used in your anus.

If you’d like to use a plug for your anus rather than a dildo, however, there are some excellent choices. The Slim Jane, Lava Plugs 1 and 2, Shapely Plug, Sapphire Plug, Little Flirt and Big Flirt are all great options to use for the back end of double penetration. If you’re using as much lube as we recommend, though, none of these plugs is likely to stay put for long. The best plug for hands-free pleasure is the Tristan, which can be particularly helpful since you’re likely to have at least one hand full.

When exploring simultaneous anal/vaginal penetration, keep the angle in mind. You may need to adjust the position of your body and the toys to make sure that the two toys hit all the right spots.

Using Harnesses

Another helpful tool for double penetration is the harness. The Thigh One On, as far as I’m concerned, is the goddess’ gift to kinky girls. It’s designed to be fastened around a partner’s thigh, providing an excellent way to use those quadriceps. But it can be fastened to a couch, bedpost or other solid object, and can be a great boon if you’re trying to fill all those special places at once. The Shag Rug can be affixed to the base of the dildo (over the harness) to provide additional clitoral stimulation — which may really blow your mind.

And if you’re exploring double penetration with a male partner, the Double Trouble Harness can give him distinct pleasure of having two penises — the strap-on harness allows him to use a dildo while leaving his cock free through the lower ring. Again, you’ll run into questions of angle, since the angle of a dildo in a harness — not to mention his penis — isn’t nearly as adjustable as that of a dildo in your hand. But who knows? Anal and vaginal angles vary from woman to woman, so you might find that the angles are just right!

Double Penetration with Partners

Speaking of partners, having one or more of them opens up even more possibilities for double penetration. First, even if you’re not going to involve a male partner’s anatomy, when it comes to DP four hands can definitely be better than two. Try these tips when playing with a partner:

• Lie on your stomach so you can use your hand to control the dildo in your vagina while he or she uses one in your anus — or, if he’s male, uses his penis to penetrate you.
• Alternately, you can lie on your back with your hand tucked behind, giving you control over the rear dildo or butt plug while your partner enters you from the front with a toy or a penis.
• If you know you want to be penetrated anally by your partner, have them lie on their back and sit on top. On top, you control both the anal penetration (with your own movements) and use your hand to play with a dildo or vibrator vaginally. This way, you call the shots on all fronts, can rock back on his/her cock while playing with your pussy, and choose the movement and rhythm you prefer.
• Lying on your side can make things even easier.
• If you’re using a Thigh One On, your partner can slide his or her thigh between your legs to give that dildo — anal or vaginal — more thrusting power. And there’s nothing that says you can’t use two of these harnesses next to each other. The previous cautions about angles still apply.

If you’ve actually got two partners, so much the better! If you’re using sex toys, that gives you not four but six hands, not to mention at least four thighs, to work with. If you’ve got two partners and you’d like them to penetrate you either with strap-ons or (if they’re male) with penises, keep these points in mind:

• Remember that while the positions used in erotic videos can provide some great ideas, those positions are designed so the camera can get the best possible angle. Unless you’re using your camcorder to make your own sexy videos (which is certainly an option), you’re going to be much more interested in what it feels like than what it looks like. Also, many of the porn positions are difficult or tiring to sustain; move around until you find the position that will be comfortable enough for you to relax and get off.
• Keep the relative body size of your partners in mind. Certain positions (crouching over a partner who’s underneath you, for instance) will give you more mobility and control over the penetration while still allowing a second partner to get in on the action.
• Thrusting when two partners are involved in simultaneously penetrating you can become either a daunting challenge or a synergistic, ecstatic experience. Make sure all three of you are working together to move your bodies in a way that maximizes everyone’s pleasure.
• Most importantly, remember that the most critical rules of anal sex apply — appropriately enough — doubly here. Go slow, stop if it hurts and use a lot of lube! It’s quite possible that you’ll need to use more lube than you normally would, because there’s likely to be a lot of extra friction.

Lastly, keep in mind that double penetration is such a huge erotic fantasy precisely because it’s something acrobatic and challenging. If it proves not to be something that works for you — or your partner(s) — in real life, it can still remain a cherished fantasy. Certain bodies just don’t fit together in certain ways, so be open to experimenting and trying new positions and styles.

Have fun!

I know tonight’s the night. It’s a Friday night; both of us had long days at work. While you’re downstairs making dinner, I take a long hot shower, feeling my muscles relax and my pulse quicken as I think about what I’m going to do to you tonight. I step out of the shower, towel dry and take out the strap-on harness. As I fit the dildo into place and step into the harness, I picture you splayed before me, taking my cock into your ass. I can feel the pulse of my pussy as I buckle up the straps of the harness.

I put on a t-shirt without a bra and a faded pair of jeans just tight enough to display the long, hard bulge plainly in front. I go downstairs to the kitchen, where you’re chopping vegetables. Your butt looks so good in those boxer shorts you’re wearing; I get more excited as I come up behind you, put my arms around you, and grind my crotch against your ass.

You tense against me, then relax. I put my lips very close to your ear and breathe warmly. “I’ve got a very special surprise for you tonight,” I tell you, just as you realize what the bulge against your ass means.

You catch your breath, squirm against me. I reach down under the counter and feel your cock swelling in your boxers. I smile and kiss your neck, satisfied that I’ve had the desired effect. I back off and go into the dining room to set the table.

All through the delicious dinner, I can see the anticipation and nervousness on your face. I can see you shifting uncomfortably on your seat.

When we’ve both finished, I smile and ask if you’d like to watch some TV. You catch my drift right away; we go into the living room and recline on the couch. You seem to be paying extra attention not to touch my crotch — maybe a little frightened of it? But I can see that your cock is half-hard under your boxers.

You pick up the remote and ask what I’d like to watch. “Start the VCR,” I tell you, and you do. The wide-screen TV is filled with an image of a gorgeous guy down on his knees, using his mouth on a woman’s strap-on. I feel you tense again. I put my arms around you and kiss your neck.

I’m a little afraid I’ve gone too far too fast; after all, I’ve done this before many times, and you haven’t. “Shhhh,” I tell you soothingly. “Don’t worry, I’ll go slow.” You seem to relax, knowing I’ll take care of you.

We lean into the couch and begin kissing, my nipples hardening under the t-shirt as you run your hands over them. I stroke you through your shorts, feeling an overwhelming urge to bend over and take your hard cock in my mouth. But no, tonight I’m the one who’s going to get sucked and do the fucking. Your hands feel good on my breasts, but I take one of your wrists and push your hand down into my crotch. Your fingers curve around my bulge, stroking it as if it were a real cock. I moan softly as if it was; the feel of pressure on the base of the dildo is as sexy to me as your mouth on my pussy would be. I stroke your cock as you stroke mine — and then, to my surprise, you bend down and unzip my pants.

It’s been a long time since I had a lover who was willing to play this way with me; I feel my pulse pounding as I watch you taking out my rubber cock and sucking it. I coax you on with dirty words: “Oh, yeah, you look so good sucking that… you’re so pretty with your mouth around my cock.” The dirty talk seems to heighten your interest, and you slip your hand down between the straps of the harness to work two fingers inside me, pressing up against my g-string. I run my fingers through your hair as you bring me closer to orgasm, getting still closer when your thumb works its way under the base of the dildo and presses my clit. I could almost believe my cock is real, that you’re sucking me off and I’m about to come in your mouth. The thought sends an explosion of hunger through me and I come, unexpectedly, all of a sudden, in an intense rush of sensation. “Oh yeah,” I tell you. “I’m coming in your mouth. Swallow it…”

But I’m far from satisfied; my cock doesn’t get soft when you suck it off. Rather, my appetite for more of you has been heightened, and I guide you onto your back so I can lift your legs up over my shoulders and raise your ass off the couch. I put my mouth on your balls, totally ignoring your cock though my mouth is watering for it. But tonight I want to pleasure you another way.

I lick lower and part your cheeks gently, reaching down to take the dental dam from where I’ve placed it under the couch, getting it out of the plastic bag, stretching it between your cheeks. My tongue finds your musky, puckered hole, wriggling inside as I feel it loosening up. You moan as I lick my way up and down your crack. I can tell you’re ready for me, and I smoothly reach under the couch to where I’ve stashed the towel and the lube. I spread the towel on the couch, then lean back and look at you.

“You want this?” I ask, glancing down at my cock.

You nod, hungrily.

“If you want to get fucked, get up on your hands and knees.”

You do it, positioning yourself over the towel the same way I’ve done more times than I could count. You gasp as you feel the cold dribble of lube between your cheeks; I rub more of it on my hand, warming it before sliding one finger into your asshole. You’re really very tight; it excites me that you’ve never done this before. I put more lube on the head of my cock and rub it all over, then gently nuzzle my cockhead into the cleft between your buttocks.

I use one hand to guide the dildo and one to reach under you, stroking your cock as I press into you. “Breathe out,” I tell you, and push the head in; you take a sharp breath as you feel it popping into you. I’ve selected a particularly small dildo, but it’s still a big step for someone who’s never been fucked like this. I feel your muscles tense underneath me; then slowly you relax and I sink into you, stroking your cock as mine enters you all the way.

Hearing you moan like this makes me turned on all over again. I could easily make myself come, but now I’m more interested in feeling your cock surge and spurt in my hand. I lift myself up with one foot on the couch so I can have more control as I slowly give you my cock, stroke after stroke. I hear nothing but pleased noises from you, but I’m very careful to go slow — however much I want to fuck you harder and harder until you scream.

The whole time I’m fondling your cock, feeling it hard in my grasp, feeling dribbles of pre-come running down from the head. It would be easier if I made you stroke yourself, but I want to feel it as you come with my cock inside you. I hear your breath quickening. I pump your cock harder, sensing your anus loosening as you relax into the sensations, then tightening as you get closer to orgasm. Then, all at once, I realize you’re at the point of no return. Your body shudders, your cock throbs and spurts in my hand. I keep stroking, in and out of your ass, back and forth on your cock, until I hear a gasp from you and know you need me to pull out. I gently ease back, waiting for your tightened anus to release me of its own accord. My cock slips out and you let out a relieved sigh. I lay down on top of you, feeling you slump onto the couch. I rest my cock in the curve of your ass as I nuzzle your neck and whisper, “Now you’re mine.”

I know tonight’s the night. It’s a Friday night; both of us had long days at work. While you’re downstairs making dinner, I take a long hot shower, feeling my muscles relax and my pulse quicken as I think about what I’m going to do to you tonight. I step out of the shower, towel dry and take out the strap-on harness. As I fit the dildo into place and step into the harness, I picture you splayed before me, taking my cock into your ass. I can feel the pulse of my pussy as I buckle up the straps of the harness.

I put on a t-shirt without a bra and a faded pair of jeans just tight enough to display the long, hard bulge plainly in front. I go downstairs to the kitchen, where you’re chopping vegetables. Your butt looks so good in those boxer shorts you’re wearing; I get more excited as I come up behind you, put my arms around you, and grind my crotch against your ass.

You tense against me, then relax. I put my lips very close to your ear and breathe warmly. “I’ve got a very special surprise for you tonight,” I tell you, just as you realize what the bulge against your ass means.

You catch your breath, squirm against me. I reach down under the counter and feel your cock swelling in your boxers. I smile and kiss your neck, satisfied that I’ve had the desired effect. I back off and go into the dining room to set the table.

All through the delicious dinner, I can see the anticipation and nervousness on your face. I can see you shifting uncomfortably on your seat.

When we’ve both finished, I smile and ask if you’d like to watch some TV. You catch my drift right away; we go into the living room and recline on the couch. You seem to be paying extra attention not to touch my crotch — maybe a little frightened of it? But I can see that your cock is half-hard under your boxers.

You pick up the remote and ask what I’d like to watch. “Start the VCR,” I tell you, and you do. The wide-screen TV is filled with an image of a gorgeous guy down on his knees, using his mouth on a woman’s strap-on. I feel you tense again. I put my arms around you and kiss your neck.

I’m a little afraid I’ve gone too far too fast; after all, I’ve done this before many times, and you haven’t. “Shhhh,” I tell you soothingly. “Don’t worry, I’ll go slow.” You seem to relax, knowing I’ll take care of you.

We lean into the couch and begin kissing, my nipples hardening under the t-shirt as you run your hands over them. I stroke you through your shorts, feeling an overwhelming urge to bend over and take your hard cock in my mouth. But no, tonight I’m the one who’s going to get sucked and do the fucking. Your hands feel good on my breasts, but I take one of your wrists and push your hand down into my crotch. Your fingers curve around my bulge, stroking it as if it were a real cock. I moan softly as if it was; the feel of pressure on the base of the dildo is as sexy to me as your mouth on my pussy would be. I stroke your cock as you stroke mine — and then, to my surprise, you bend down and unzip my pants.

It’s been a long time since I had a lover who was willing to play this way with me; I feel my pulse pounding as I watch you taking out my rubber cock and sucking it. I coax you on with dirty words: “Oh, yeah, you look so good sucking that… you’re so pretty with your mouth around my cock.” The dirty talk seems to heighten your interest, and you slip your hand down between the straps of the harness to work two fingers inside me, pressing up against my g-string. I run my fingers through your hair as you bring me closer to orgasm, getting still closer when your thumb works its way under the base of the dildo and presses my clit. I could almost believe my cock is real, that you’re sucking me off and I’m about to come in your mouth. The thought sends an explosion of hunger through me and I come, unexpectedly, all of a sudden, in an intense rush of sensation. “Oh yeah,” I tell you. “I’m coming in your mouth. Swallow it…”

But I’m far from satisfied; my cock doesn’t get soft when you suck it off. Rather, my appetite for more of you has been heightened, and I guide you onto your back so I can lift your legs up over my shoulders and raise your ass off the couch. I put my mouth on your balls, totally ignoring your cock though my mouth is watering for it. But tonight I want to pleasure you another way.

I lick lower and part your cheeks gently, reaching down to take the dental dam from where I’ve placed it under the couch, getting it out of the plastic bag, stretching it between your cheeks. My tongue finds your musky, puckered hole, wriggling inside as I feel it loosening up. You moan as I lick my way up and down your crack. I can tell you’re ready for me, and I smoothly reach under the couch to where I’ve stashed the towel and the lube. I spread the towel on the couch, then lean back and look at you.

“You want this?” I ask, glancing down at my cock.

You nod, hungrily.

“If you want to get fucked, get up on your hands and knees.”

You do it, positioning yourself over the towel the same way I’ve done more times than I could count. You gasp as you feel the cold dribble of lube between your cheeks; I rub more of it on my hand, warming it before sliding one finger into your asshole. You’re really very tight; it excites me that you’ve never done this before. I put more lube on the head of my cock and rub it all over, then gently nuzzle my cockhead into the cleft between your buttocks.

I use one hand to guide the dildo and one to reach under you, stroking your cock as I press into you. “Breathe out,” I tell you, and push the head in; you take a sharp breath as you feel it popping into you. I’ve selected a particularly small dildo, but it’s still a big step for someone who’s never been fucked like this. I feel your muscles tense underneath me; then slowly you relax and I sink into you, stroking your cock as mine enters you all the way.

Hearing you moan like this makes me turned on all over again. I could easily make myself come, but now I’m more interested in feeling your cock surge and spurt in my hand. I lift myself up with one foot on the couch so I can have more control as I slowly give you my cock, stroke after stroke. I hear nothing but pleased noises from you, but I’m very careful to go slow — however much I want to fuck you harder and harder until you scream.

The whole time I’m fondling your cock, feeling it hard in my grasp, feeling dribbles of pre-come running down from the head. It would be easier if I made you stroke yourself, but I want to feel it as you come with my cock inside you. I hear your breath quickening. I pump your cock harder, sensing your anus loosening as you relax into the sensations, then tightening as you get closer to orgasm. Then, all at once, I realize you’re at the point of no return. Your body shudders, your cock throbs and spurts in my hand. I keep stroking, in and out of your ass, back and forth on your cock, until I hear a gasp from you and know you need me to pull out. I gently ease back, waiting for your tightened anus to release me of its own accord. My cock slips out and you let out a relieved sigh. I lay down on top of you, feeling you slump onto the couch. I rest my cock in the curve of your ass as I nuzzle your neck and whisper, “Now you’re mine.”

If everything’s gone swimmingly, you might want to expand your technique, adopt new tools and help your man enjoy new forms of anal pleasure. This third — um, entry — will cover anal penetration of men with dildos, anal beads, butt-plugs, and vibrators. I’ll also say a word or two about oral-anal pleasure.

The most important thing to remember is, as I’ve said before, anal sex is not a goal-oriented activity. All anal play does not have to proceed to penetration. The exterior of the anus is very sensitive, and you can have hours of fun just playing with it.

But if he’s enjoying himself and you’re enjoying yourself and you both — um, dig — the idea of deeper exploration — then on with the show.

Rimming

First, a word about rimming. Some of you may be wrinkling your noses, but almost anyone who enjoys anal sensation and has had the pleasure of being rimmed will tell you that it feels incredible. For the giver, it can be a lot of fun, as well. In one sense, it’s vaguely similar to cunnilingus — but you can do it on a boy as well as a girl!

Unfortunately, rimming isn’t the safest activity in the world. Though it’s relatively low-risk for transmission of HIV, it’s a high-risk activity for transmission hepatitis A, B and possibly C (which are collectively much more common than HIV — and much, much easier to transmit), as well as intestinal parasites and a whole host of other sexually transmitted diseases.

That’s why the kitchenware manufacturers of the world thoughtfully invented plastic wrap. Well, maybe it’s not why, but that certainly is a nice image, isn’t it? Place a dab of lube on his anus, spread some plastic wrap between his cheeks, and have as much fun as either of you can stand. Another option are Dental Dams and the thinner (and therefore more sensation-transmitting) Glyde Dams. Plastic wrap, however, has the advantage of being dirt cheap and not tasting like anything. You can also spread oil-based goodies like whipped cream on the wrap (your side of the wrap, silly, not his) to provide you with hours of tasty delight as you explore his sensitive side. Dental dams aren’t safe for use with foods that contain oil.

If you do rim without protection, ask him to wash well with soap and water — and rinse well (unless you actually like washing your mouth out with soap). Afterwards, rinse your mouth with antiseptic mouthwash. You can still catch many very nasty things, but these two measures will lessen your risk substantially.

Lubricant

I keep saying this, but it’s really, really important. You don’t want to end up in the middle of a hot and heated session and run out of lube. Not everybody prefers thicker lubes for anal play, but they’re a good idea when you’re just starting out, because they provide a little more cushion. Thick lubes like For Play Lube deluxe Cream, Embrace, or Slippery Stuff Gel are excellent for anal play.

The silicone-based Eros Lube can be a nice change of pace, but remember not to use it with cyberskin or silicone toys — it’ll ruin them. Similarly, don’t ever use an oil-based lube like Men’s Cream, petroleum jelly or baby oil with latex toys, since they will slowly dissolve the toys (as well as any condoms, gloves or dental dams they touch). In any event, petroleum jelly tends to dry out anal tissues, and baby oil is too thin to be ideal for anal play. Neither are recommended.

The Prostate

Many guides to male sexuality ignore the prostate, which is a mistake. It’s a walnut-sized gland several inches inside the rectum — the depth varies from man to man, but you can sometimes reach it with your fingers; other times a dildo is required. Women don’t have a prostate — but, in fact, it’s theorized that the prostate is the male equivalent of our G-spot, so it won’t surprise you to hear that many men experience mind-blowing sensation and even orgasm from prostate stimulation.

If you find his prostate for the first time, I would advise you to be gentle — poking it indiscriminately can hurt. But gentle stroking can drive him out of his mind. Remember that not all men enjoy prostate stimulation — anal play can feel great without it. But many men really, really love it.

Anal Plugs

As I mentioned in the last column, fingers are not exactly the smoothest part of the human body. Therefore, even if fingers didn’t feel good inside his butt, a narrow anal toy like the small Majestic Plug, the Slim Jane, the Little Flirt, or the petite Shapely Plug can feel great, since, conveniently enough, they come without fingernails, calluses, or knuckles. The Little Flirt has the advantage of being silicone, so you can boil it to disinfect it before and after use. If you prefer to use a condom to keep your plug clean, you can pull the end of the condom over the base of the plug and tie it, or cut one of the fingers off a Latex Glove and stretch it over just the insertable part of the plug.

Another point about butt plugs is that they’re a little misnamed. They can be left in the anus if you like while you go about other delicious business, but in my experience they don’t always stay put without a hand, surface or harness to hold them in. This is especially true of smaller plugs, making them better adapted to play with the same way you would play with a dildo. The silicone (and festive-hued) Tristan Plug definitely stays put — but it’s a little wider than some beginners will want to try.

Whatever you insert into his butt, be absolutely sure that it has some kind of flange or base wider than the inserted part. Unlike the vagina, the anus is deep, and it’s easy for non-flanged toy to slip in there. It sounds silly, but you’d be surprised how easy it is to lose hold of something when your hands have half a bottle of lube on them.

Vibrators

Vibrators can be especially fun for beginning anal explorers. The vibrations tend to relax the anus, making penetration easier — and just generally feeling damn good. Not everyone likes them, but given the availability of inexpensive vibrators, they’re definitely worth a try. Again, make sure that you use a vibrator with a flange or attachment at the base so it doesn’t slip all the way inside his butt. If a vibrator slips in there when it’s turned on and you can’t get it out — that really means a trip to the emergency room, and fast. The heat generated by the vibrator’s motor can cause serious problems.

The Scorpio is Good Vibrations’ most popular vibrating toy for anal beginners. It’s relatively inexpensive, thin and easy to insert. Other great vibrating anal toys are the Arrow Twist Vibe and Ruby Vibro Plug. The Red Rider Plug has the added advantage of having two thicknesses you can play with, so it’s splendid for beginners.

Remember never to put a vibrator like the Smoothie in his butt because — you guessed it — it doesn’t have a flange. Smoothies can feel great on the outside of the anus, however.

Anal Beads

Other good anal toys to try are Bubble Beads and Anal Beads. Both of them are relatively small in diameter, but their geography will usually require you to insert them with fingers inside the anus, so they’re probably not the best toy for absolute beginners. The usual concept behind anal beads is that you insert all or most of them, then pull them out either one at a time or all at once, quickly, just as he reaches orgasm. There’s nothing that says you have to use them that way, but I’ve had rave reviews of that technique from more than a few male friends. If you’re going to try that, though, use lots of lube, since whipping out an insufficiently-lubricated set of grape-sized friendlies will put a major buzzkill on that orgasm he’s having.

Dildos

As with all anal play, it’s a good idea to start small. That’s not to say men don’t like big things in their butts — in fact, a lot of them like very big things in their butts. But with a recipient who’s new to anal penetration, it’s best to be conservative. “That feels so good, I want more!” is so much sexier than “Owwwwwwwwwwch!” or “Get away from me with that monster!”

Again, be sure that any dildo you put in there has a base substantially wider than its shaft. It is not fun to go fishing around for something that’s slipped out of your hand, and if something really gets stuck up there, it means a trip to the emergency room.

Silicone dildos like the Rex and Hot Rod tend to be a little more rigid than non-silicone toys, making anal penetration a little easier in some peoples’ opinion. Non-silicone dildos like the Pearl Jelly Dildo, the Jelly Jewel Amethyst or the Duke, on the other hand, tend to be cheaper, meaning you can try different sizes and shapes without cashing in your stock options. Latex toys can’t be boiled, but you can keep them clean with condoms, or by just scrubbing them down with antibacterial soap after use. They also tend to collect lint, so you might want to rinse them before use.

Many dildos look like penises. If your man is squeamish for any reason about enjoying a dildo that looks like human equipment, some excellent “non-representational” dildos are the Babe, Queenie, Silk and Willow.

Again, go slow — in-and-out isn’t necessarily the end-all-be-all, any more than it is with you. He may like in-out-repeat a lot, or he may just prefer the feeling of fullness that comes from having a dildo inside him. Either way, he may enjoy it if you stroke or kiss his penis and the rest of his body, keep eye contact with him, and/or tell him exactly how sexy he looks with his legs spread and a dildo in his ass.

If he loves this more than either of you ever dreamed he would and finds himself hungry for more, more, more — remember, there’s always Randy. He’s very friendly, but I wouldn’t suggest bringing him along on a first date.

Next installment will deal with strap-on dildos, double dildos, and what to do if you’re lucky enough to have one of those lucky anal invaders with a flesh-and-blood penis, also known as a man.