First thing to know about any anal play, strapped-on or otherwise, is patience, patience, lube, patience, more lube, and even more patience.

Remember that our eyes are bigger than our orifices, so start small and work your way up; a good anal session will generate a fun pile of mementos scattered nearby when you're done. My favorite anal toy of all time is my finger... especially with a latex glove on it, poof! no finger nails! and easy clean up! Just reverse out the glove and your hands are clean and ready to go on to the next thing. Get started by having your partner use lube and massage just the opening of the butt... don't even worry about going in the first few times you play there (remember, patience means that you might not cover all of these steps in one session... let your body tell you when you are ready for the next step).

Once massaging the opening starts to feel good, then she can either slip in just the first part of her (lubed!!) finger, or the first bulb of the (lubed!!) Small Ripple (the first toy I suggest to people that have never played “back there”). I like the Small Ripple because even used full-tilt, it's not much longer than a finger, and the bumps do good things when worked in and out. I'm serious about lube with any anal play; the anus isn't naturally lubricating so you have to lube more than you'd think, then lube again).

After the Ripple is feelin' good, you can move to the toys in the kit, or other toys that are on the small side of the scale. I like ones with curves and bumps, all of which are great for hitting the elusive prostate, the gem of the human body... more sensory nodes than just about any other place else on the male body...

Now that your butt is happy having things in it... let's attach said 'things' to your partner. My favorite way to do this is with the harness that comes with the Bend Over Beginner Kit by Tantus Silicone... it's comfortable, machine-washable, and very durable. It's also super-duper adjustable, and once she's figured out how much strap she needs she can trim off the extra and burn the edges so they don't fray.

For an extra bonus prize, has a sewn-in tunnel for the included mini-vibrator so that your harness is instantly both vibrating panties and vibrating the dildo. I've washed mine a bunch of times and it still looks new. I also like to remove the purple pad and get a guy to wear it... so that he has 2! Good times. The Bend Over Beginner Kit comes with 2 simple dildos, I started by wearing the larger one and using the smaller one to warm up my partner. You can also buy the harness separately if you already have a stock of small dildos to use with it.

Remember, no one is trying to say that strap-on play isn't just plain weird. It will feel unnatural for both of you at first, because she's going to have to make opposite movements than she's used to, as will you... just laugh about it and embrace that it's an adventure.

The first man I used a harness with and I were both "virgins" to it and we stumbled though it with a laugh. My biggest problem was that my legs (when kneeling) were shorter than his, so I couldn't get lined up right. I always ended up with 3 or 4 inches left over between us (I just couldn't figure out how to close up that gap), because I couldn't line things up correctly. That's why the next toy I reach for is the Spike; it's smooth and easy entry because of the small tip, and it's long enough that she can just use the tip of it and have room to spare so she has some working room.

Once you've got the receiver used to something a bit wider and longer, you can move up to my favorite dildo of all time, the Charmer. It's got pronounced ridges all the way down one side, which makes it grrrrreeeeeat for anal play because it hits the prostate just like it does the g-spot for us... over and over and over and over with each bump, with each movement, both on the way in, and again on it's way out. Life is good...

There's a mini-vibe in the kit that can be inserted in the tunnel on the harness... presto! vibrating panties, and a vibrating dildo at the same time. The vibration doesn't do much for girls when inserted (the vagina only feels vibration for the first 1.5 inches... after that, it only responds to pressure), but the prostate loves it, so in a girl/boy situation this vibe set up is perfect, vibrating panties for the wearer and prostate stimulation for the man.

Remember, everyone's sexual tastes are different, so none of these guidelines are hard and fast. My first harness play partner liked me to work up to moving pretty quickly, almost like regular sex... I liked either being doggie style so I could reach around and play with him at the same time, or missionary (a little more awkward, but there's something to be said for being face to face, no?) and then I could reach his goodies even easier.

My second harness partner was experienced with it and taught me some more things... the best one: pay attention to whether there is lube further in. I would lube the opening and once the dildo got past that lube there was none. That's when gloves come in handy... you can do the lubing deed and not have to get up and wash your hands afterwards (just reverse them out and presto! Clean hands!).

He also liked much slower movements than #1, barely moving, really, as he was much more sensitive than #1. The moral of that story each couple will find what's right for them, there's no right or wrong here, and don't expect it to work as easily as it does when the roles are reversed. Remember that you each have years of experience moving the opposite way, so it will take some time to get used to moving “backwards.”

Pretty simple, really... just remember, patience, lube, more patience, more lube, and to laugh a little... it's an awkward act at first, but OH SO worth it when you get the hang of it.

Oh, and don't forget to HAVE FUN!!