Okay boys, here are the down and dirty things you need to know to get her to let you give it to her “back there.” Most women are probably like me, they have had guys begging them to let them do it, and a few have tried it once or twice to discover that it is painful. Pain is not a requirement of anal, and that is something that people need to know. Now boys, if your girl has had one of these experiences, she is going to be even more reluctant to let you do it. My biggest suggestion is to be patient. Don’t ask her while you’re in bed, and hope that she’ll turn around and offer it up to you like a birthday present. It probably won’t happen unless she has done it before and liked it.
And she can like it, all it requires is a little sensitivity on your part, and a willingness to follow a few simple directions. I will dispense my advice on this subject now.
1. Tell her that you fantasize about it, but don’t ask her to do it– not yet. Hearing you talk about it will put thoughts in her head without making her feel pressured or nervous.
2. Many of you will not like this one, but here it is: ask her to do it to you. I’m not suggesting you buy a strap-on or anything, although if you are into it, great– I’m talking about asking her to just put her finger up there. Tell her how great it feels, and how much you love it.
Before you let her do this to you, allow me a few personal preference related suggestions. Wash yourself well, and make sure you don’t need to “drop the kids off at the pool” anytime soon. This is a messy and unpleasant discovery for any woman (okay, most women). Furthermore, buy yourself an anal douche, if you want one a bit more cheaply (anytime it is marketed as a sex product the price shoots up a thousand fold), you can go to your local pharmacy and buy an enema kit or bag. This will ensure that your colon is empty and clean before you proceed. I know, an unpleasant thought, but let’s be real here for a moment: we all know what comes out of there, don’t we?
3. Use a lot of lubrication, your choice here, but ensure that you are using enough. Then ask her to insert her finger in your ass. Don’t say it like that. “Darling, would you do me the courtesy of inserting your digit into my rectum?” won’t do you, her, or the mood any good. Say something sexy; “I want to feel your finger inside me,” works well for me, it isn’t crass, but doesn’t leave a lot to the imagination.
4. Once you have conquered her fears in this area, try suggesting the same for her. Start small gentlemen! You generally have larger fingers than we do, and if you scare her or hurt her now, you’ll be SOL. Go slowly and gently and, trust me, once she gets over her initial embarrassment, she’ll be purring and moaning under your ministrations.
5. Purchase an anal dildo. Okay, I can see where this might be an uncomfortable purchase for you to make. Nothing says awkward like walking to the woman at the counter with an object that screams “I love it in my ass.” Nonetheless, suck it up and do it. Or order it online if that is easier for you to deal with. Make sure it is somewhere between the size of your largest finger and your erect penis. You may even want to purchase something like the Doc Johnson Anal Tool– it has increasingly larger bulbs on it to help stretch her although it’s purpose is really more about the sensation.
6. Give it to her as a gift, but not in the bedroom. Let her think about it, dwell on it, anticipate it. If you have done everything right up until this point, she’ll be thinking about the potential for enjoyment rather than fearing the thing.
7. Speaking of letting her think about it, you want her to be really turned on. I mean really. Any anxiety or tension in her body will make her tighten her sphincters making the whole thing fairly difficult and unpleasant.
8. Once you have her moaning in exquisite pleasure, start to use the anal dildo with her. The purpose here is to increase the stretching capacity of her anus, while making her relax, knowing it won’t be painful. Don’t do any of the porn moves– the hard thrusting, the really deep insertion– save that until you are both experts.
9. After a few experiences with the dildo, you may be ready to try the real thing. Once again, make sure she is really turned on. She should be dripping with need before you go anywhere near her backdoor with your member. Go down on her, describe your fantasies, tell her all about what you want to do. If you can, make sure she has an orgasm before you go for it; this ensures greater relaxation as well as higher levels of specific “feel good” hormones coursing through her brain.
10. Lube well. And then, lube again. I cannot emphasize the necessity of this enough. Use your finger to work it up inside her, and make sure you are coated fully. Now, start slow, with just the tip, and gently, GENTLY I SAID, work your way in. This may not be the night to achieve complete penetration, it may be another few nights until you are able to do any real thrusting, but trust me, the results are worth it. You want her to enjoy it as much as you do. If she doesn’t, you ain’t getting’ it again baby!