If you’ve been following along with this series of articles on helping your wife/girlfriend learn to enjoy anal sex, you’ll realize that we’ve made a fair amount of progress. In the first two entries, we focused on helping her come to view her “rear entry” as an erogenous zone. If you’ve been successful in following the instructions so far, she should now realize that it can be a source of pleasure for her when she has sex. Hopefully by this point you’ve repeated our last exercise (penetrating her anus with your finger during oral sex) multiple times, and it’s now something she looks forward to.

Roger, the fictional protagonist we’re using to illustrate these instructions, definitely feels encouraged. His wife, Alison, who had originally viewed anal sex in a negative light, now seems to very much enjoy having his finger inserted inside her ass when he goes down on her. In fact, it seems to make it easier for her to climax, and the mere fact of adding this move to their repertoire has already added a missing element of pizazz to their sex life. However, he’d like to do more. He’s still got his sights set on his ultimate prize, and that means that they need to get beyond placing just a finger up there!

This next step will allow both Roger and you to do that. Before I go into detail, however, I should let you know that this step is somewhat optional, and you’ll need to make a judgment call on whether you think it is necessary. It’s possible that after the work you’ve done together so far, your wife has already reached a point where she’s curious about anal sex, and would be open to the idea of trying it with no further preliminary steps. If you believe that this is true, then you may decide to skip this step and proceed on to the instructions in the fourth article of this series. However, if you think there’s any risk, or even if you just think it might be fun to leverage anticipation a bit more, I recommend that you proceed with the directions I’m about to lay out. In other words, it’s safer to do this step, but if you really think it’s not necessary, the choice is yours.

One of the concerns many women have about anal sex is the idea of putting something relatively large into a little opening. So far, we’ve avoided this issue, as the largest object we’ve involved is a finger. If you’re going to get to full-fledged anal sex, though, you’ll have to face and overcome this obstacle at some point. The reality is that, unless you’re built like Goliath, your wife or girlfriend’s anus can readily accommodate your penis provided that the proper preparations are made. The challenge you have to overcome, then, is mostly mental—your wife has to know and believe that she can handle you in order to feel comfortable.

To overcome this challenge, we’re going to use a toy made for anal insertion—a butt plug. A butt plug, if you’re not familiar, is somewhat like a dildo, but made for use in the rear end. There are many kinds to choose from! I’d recommend, however, that you look for one for beginners—that means that it shouldn’t be too large in either length or especially width. Read the descriptions when you shop for one and watch for words like “beginner”, “first-time” or “trainer”. Another option you might want to consider is purchasing a vibrating model. These work well, and absolutely will amp up the sensation for your wife when you insert it. I’m repeating myself, I know, but again, be sure you don’t get something that is too large!

You should also definitely pick up some sort of lubricant to use with the butt plug! I highly recommend that you select a type that is made specifically for sexual use—don’t just pick up some Vaseline at the supermarket. A good brand is “Astroglide”, but there are many varieties to choose from. Look for something that is recommended for anal play.

You have so many options on where to buy both of these items online that I’m not going to try to provide a list of recommendations. If you’d like to get my thoughts on vendors of online sex toys, you can visit my review page. Any site listed on that page ought to be able to fulfill your needs.

So, go ahead and place your order. I’ll wait until it arrives…

Once you have your butt plug and lubricant in hand, you’re ready to begin. Select a night when your wife/girlfriend is “in the mood”, and make sure that you have both the plug and the lube close at hand, but out of obvious sight. Spend some time on foreplay to ensure that your lover is highly excited! When you judge the moment is right (now that you’re experienced!), insert your finger into her behind as you give her oral sex. However, after a minute, stop and tell her that you want to try something new.

If she asks, or if you feel it’s best to give her advance warning, tell her that you have something that’s made to go into her butt. Then, apply a drop or two of the lubricant to her anus, and slide your finger back into her. Make sure that the lubricant gets inside her—use your finger to put it there. Just leaving it outside won’t work nearly as well. Position her properly to be able to receive the plug—if she’s on her back, this means you want to raise her legs up over her head to make her rear end highly accessible.

Then, take the butt plug and slowly, gently, insert it into her. You might have the best luck by pressing it into her a bit at a time, with a gentle thrust, then a pause, then another thrust, another pause, etc. If it starts to hurt her, take a break and use your tongue to give her pleasure. Check to make sure you used enough lubricant, and consider adding some to the sides and end of the plug. Then start again. Assuming you got something small and appropriate for beginners, you should have little trouble inserting the plug deep inside her.

Once it is in, make sure you take your time and give your wife the very best oral sex of her life. If you got the vibrating kind of plug, turn it on a minute or so after you insert it. That will simply add to the experience for her. If at all possible, bring her to orgasm this way. You want, as always, for this to be a highly pleasurable, highly memorable experience for her—one that will create an association in her mind between having something large in her ass and erotic bliss.

Assuming again that you purchased a smaller model plug, you can go ahead and mount your wife and have vaginal intercourse with her while it is still inserted. Again, this will reinforce the idea that it is a good thing to have something in her ass while having sex.

The bottom line, whatever you do, is to make sure your wife or girlfriend has an outstanding time while you have the plug inserted in her. When you both are done, wait a little to let her recover, then gently help her to remove the plug. Stay with her to cuddle for some post-coital bonding time. Again, you want to be sure that the whole experience is positive. Then, after you get up, be sure to clean the plug properly (often they will come with instructions on cleaning) so that it’s ready for use next time.

And you should definitely use it again! I’d suggest giving her rear end a rest for a time or so to allow her to recover, but then break it out again. With any luck, she’ll be eager to take the plug for another spin around the block!

Okay, after this, the next step is going to finally be true anal sex. You’ve laid all the groundwork, helped your wife or girlfriend become used to being anally penetrated, and now inserted a larger object into her ass and helped her to truly enjoy the experience. You’re ready…she’s ready…Roger’s ready…

Roger? Oh, yes. When Roger broke out the lubricant and plug, Alison didn’t really know what to think. But his tongue and finger felt so good, she was willing to open herself up and give it a try. The lubricant did its job nicely—Roger’s finger moved in and out of her ass, spreading the lube around inside. She felt the tip of the plug press up against her, and then a gentle pressure, and then…she felt it slide up and in.

Alison’s breath caught in her throat as the plug slid past her entrance and deeper into her than Roger’s finger had ever gone. Roger stopped with it halfway in, then moved it forward bit by bit, each bit accompanied by an exhalation from Alison, until it had fully entered her. Alison came almost immediately when Roger began to lick her, then again a few minutes later. When Roger moved up on top of her and entered her vagina, she felt so full…

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