Communication, being 100 percent straightforward about the fact that I will fuck your ass, but in a nice way. This includes nonverbal communication (such as always touching the asshole before I ever touch the pussy, before you ever bring up the fact that anal sex is the fetish) and gauging the reaction. I’ve been with veteran women who already love anal, I can tell pretty quickly, and fullblown anal sex can happen quickly, I’ve done it on the first date.

But for newbies, anal virgins, and women who have had bad anal sex experiences with dudes who didn’t know what they were doing, its important to go slow, work up to it, make sure they enjoy the attention you pay to their ass when you go down on them. If sucking on the clit, also touch the rear hole. Let your tongue go down there, tease their ass before you ever try to penetrate, even with a finger. You can tell a lot by their reaction. For the virgins I just tell them, (after getting the signs they are open to it – like if they react favorably to touching, and then just a fingertip penetrating, that they are “in training.”

(In the very, very rare occasions when the woman makes it clear she doesn’t even want to be touched back there, then that will be the end of that relationship, I’ll break it off gently in the next day or two, citing sexual incompatibility) But usually she is open to the touching, the kissing, the very small penetration during PIV sex.

In that case, over the first several sessions I make it very clear that I want to fuck her ass and that she will love it when I do. But I am patient. I make it very clear that I know what I am doing and that I won’t hurt them. Around that phase, once they know I’m a devout ass man, I tell them the story of how it became my fetish, the first time I did anal, when I was 22 years old with my 35 year old college professor, and how it made me feel, every cell in my body lit up glowing in waves of color. The story is important, and letting her know that anal is what gets me off, and she will just about always accept that.

Then its little by little, with a bowl of coconut oil on the bedside table during every encounter, being open about it and not sneaky. During PIV just reaching for the coconut oil, putting some on the fingers, maybe making her taste it and then rubbing it on her asshole. Progressing up to a thumb in the ass while eating pussy. Always be working on the ass in some way when doing anything that makes her feel really good. Never eat the pussy or fuck the pussy without also applying oil and at least caressing the asshole. She will associate the anal stimulation with the good feelings of oral and PIV. Before long, a thumb in the ass during oral, while also stimulating the g-spot with fingers and sucking the clit. Lots of oil will enable you to start small fucking motions with the thumb. But always make sure she is enjoying it. Most women will come explosively with the thumb in the ass, the clit sucking and the g-spot attention. Then as time passes they will want more ass play.

When fucking PIV use the oil to get a finger in the ass, just a little at first and then when she gets used to it, deeper. After rubbing the oil all around the asshole and getting it good and slippery the tip of the middle finger is usually how I start. 95% of women will react favorably to that. Then go a bit deeper with the finger while your dick is in the pussy. Meanwhile, talk to her. Talk dirty. Tell her you can feel your dick with your finger, you can feel your dick with the finger that is in their ass. Tell her she is beautiful. While fucking, tell her how much she’s gonna love it when she finally has your dick in her ass. The words are important, combined with the actions. But stick with the one finger for that session and make sure, no matter what, that she comes with your finger in her ass several times before you move to the next step: two fingers in the ass during PIV.

Talk to her out of the bedroom about her training regiment, use humor but be firm. “wow baby you did great, you came so hard with my thumb in your ass, you’re gonna get a gold star if you keep that up. You’re gonna be the teacher’s pet…” stuff like that. Talk to her and listen to her about how she feels about it.

Then for the next step its always good to have a small anal toy handy. I’ve had great luck with the small “ooh la la” toy, break it out the next time you are fucking, show it to her, it wont scare her, its not intimidating in size or shape, and after applying the oil and opening her butt with a finger, maybe let her see you put the plug in your mouth, let her see you coat it in oil while you are fucking her pussy, then insert the toy in her butt (SLOWLY) while fucking doggy style or eating her out. Just let it set in her ass while you fuck her and eat her. She will love it and after awhile you can start fucking her with the toy gently while you work her front hole with your cock or fingers. Usually after ten or fifteen minutes of that she will be really wanting your dick in her ass (depending on your size — I’m average — if you have a big dick you will need to work up to it more slowly).

But leave her in suspense and don’t try to fuck the ass until you’ve got her so worked up she is begging for it. If you’ve worked up to it properly she will be in heaven. As a general rule during training, always leave her wanting more. Make sure you kiss her a lot when you first put your dick in her ass. Go very slow and keep kissing her. Put it in very slowly and when its all in just let it be, don’t start fucking. Kiss her deeply. It’s the intensity and intimacy that will get her hooked. If she has her eyes closed, tell her to open them and look into her eyes. Be a hundred percent present with her in that moment. Let her know with your actions that her pleasure and comfort are top priority.

When you know she is okay with it, start moving very slowly. Add more oil to the piston. The first couple times you get your dick in the ass you might need to resist the urge to come, and just let it sit there, move very slowly, pay 100 percent attention to her face to be sure she is okay. If she is showing any sign of discomfort you need to stop, and ask her how she’s doing. If she wants you to stop, then stop. Treat her like a human that you care about. It may take a few sessions of this before you can fuck full speed and blow your load in her ass.

The payoff to the slow training and the emphasis on her pleasure is unbelievable.

Tonight, for example, after a half hour of gspot massage with fingers combined with the buttplug and the clit sucking, a couple orgasms for her, I told her I would not be fucking her pussy tonight. ” Just your ass and your mouth,” I said. She loved it. She had douched her ass before dinner so it was super clean.

Later while she sucked my dick after her third anal orgasm of the evening, she was literally dripping down her legs. ‘That dick you are sucking has made you come three times tonight fucking your ass,” I told her.

The session ended with me fucking her ass from behind as hard as I have ever fucked anyone, coming as hard as I have ever come in my life (I’m 48) and then she cleaned my dick with her mouth. When it was over she told me she came so hard she went deaf for a minute.

She was an anal virgin a month ago. Nobody had ever put even a finger in there before. This stuff works.