A podcast recorded specifically for receivers that addresses their fears and misconceptions. Please listen to it alone before you listen to it with your partner, because only you can decide whether it's right for your situation.
First, communication is the key. You need to be able to ask for what you want. If you can't open your mouth and talk with your partner about sex, he is not going to magically intuit that you want to fuck him up the ass with a dildo. Take a good long look at your relationship first. Do your very best to practice Dan Savage's GGG - Good, Giving and Game. "Think 'good in bed,' 'giving equal time and equal pleasure,' and 'game for anything—within reason.'" We are not just talking about your man's willingness to explore pegging with you...we are also talking about the state of your relationship with him...think about it. And before you blurt it out there that you want to pay his lovely ass some special attention, please read the rest of this article!
Okay, ladies - Trust. Is. Huge.
I am talking about your man's ability to trust you not to out him. This is a bigger factor than you could ever imagine! For younger men whose generation is more open to and accepting of different types of sexual play, this may not be as big of a deal. But for men, say 30 and up, it can be the single largest factor holding them back from exploring pegging. Why? Because societal repercussions can be severe for men who enjoy pegging.
And even if they have a loving, intimate relationship with the woman of their dreams...what might happen if things don't work out and they part? Will she tell? Will their circle of friends find out that he likes to get fucked? Will his friends or coworkers judge him? All those people likely have the same silly misconceptions about pegging that most people do and they might not look at it as just another passionate way to have sex with your partner.
Some men decide this is too big of a risk to take; getting outed. Perhaps because of their career, their religion or perhaps they live in a very conservative community. So the challenge is for you women to swear on whatever you hold sacred that you will never, ever out your guy. And keep that promise no matter what.
You know how men supposedly brag about the sex they are having? Well I'm sure there are some men who do...but the majority actually don't. Ask around if you don't believe me. They might make crude comments about the waitress or the woman that just walked by, but they do not talk about the details of the sex they are having with their significant other.
You know how women supposedly talk about....everything? That is actually true. Women do talk about the details. And men know that. So here is my advice around pegging. Just simply don't ever tell. Make pegging a secret thing between you and your partner that you will never tell anyone, even your best girlfriend, even if you've had too much to drink. Make it a sacred thing between you and your guy so he can relax and really enjoy it without worrying about what will happen if anyone finds out...because he knows no one ever will.
So how can you reassure him that you won't tell even if you don't stay together? You make a big deal out of it. You tell him sincerely, to his face, making sure the timing is right (special dinner, just after sex, romantic moment, no one else around), swearing to him that it will be just between you two...forever. Another idea...consider giving him some compromising pictures of you naked that he can put up on the internet if you out him. That way you are both operating on trust.
There is also the kind of trust he needs to allow you to play with such a sensitive part of his body. Anal play is quite intimate. You are asking him to open up and be vulnerable, completely vulnerable. If you have received anal sex before you know how important technique is and taking thinks slow and easy. If you have not received anal sex before - please read up on it because ass play is best done after educating yourself! Here is a basic educational article for women who are beginners at male anal play.
Pegging is Not Gay
The biggest hurdle you will likely have to get beyond is the "No - that's gay" hurdle. It's like a knee-jerk reaction in many men that no one is coming anywhere near their ass...because that's just...gay. There is a sad and rather unfortunately automatic connection between male anal play and homosexuality in so many people's minds. Very common misconception that is 100% incorrect. The part of a man's body that he enjoys having stimulated has absolutely no bearing on the gender he prefers to do the stimulating. (And actually there are a fair number of gay men who never have anal sex.)
Even if pegging does not threaten their sense of sexual orientation in any way...what stops most men is the thought that other people will think that they are gay or somehow less-than in terms of masculinity because they enjoy something up their ass. For men...the blow back can be harsh. It leaves them vulnerable to ridicule, rumor and ridiculous assumptions from a largely homophobic society. Plus they certainly do not want their lovely partner to ever think that they are anything less than manly because they like ass play.
The Magic Thing to Say
Most men are pretty intensely sexual beings...if you tell them that pegging along with cock stimulation can produce orgasms 10 times more powerful than anything they have ever experienced with tons more come, most men will want to try it. I mean really, if you were a normal horny guy after hearing that could you really live the rest of your life not exploring pegging? No, I didn't think so. Few men can.
Yet as with everything...there are all different types of men. Some will be quite ready to play at the merest suggestion. Some may require a little convincing but warm up quickly to the idea. And there are indeed those men who want nothing to do with anal play...ever, period...it's "exit only" territory. Only you women out there have a sense which category your man falls into.
Remember that men are not used to receiving and being penetrated. There is a vulnerability and openness inherent in penetration that is completely new to men. Women are quite familiar with the feeling of being penetrated during sex. For men it's a whole new deal. And that level of vulnerability can be pretty scary, surprising, and amazing all at once. Often that vulnerability is part of the turn-on for men, but that doesn't necessarily mean it is easy for a man to go to that space or that it is comfortable for him to be seen there. Being able to trust that the woman understands this role reversal and will not suddenly judge him when he softens and receives helps him to more fully relax and allow that vulnerability to happen. Promise him that you will handle his ass with care!
Semi-Guerrilla Ass Play
Many guys get interested in anal because a creative woman slid a well-lubed finger up their ass during a blow job with quite good results. This does present a way to introduce your guy to anal play...even if it's a little sneaky. I don't ascribe to the sneak-it-in-there theory...but I have heard many a man say that this is exactly how they discovered that something up their ass really turns their crank. The part of this idea that really works is that prostate stimulation generally feels best when a man is already really turned on. But... instead of sticking your finger where you do not yet have permission to go, wait until he's very close to coming and just circle your finger around the opening of his anus and see what kind of a reaction you get. The more turned on he is by your blow job the more likely you will get a good response. If he's not giving you any signals and you're not sure whether he likes it, ask him!
If your guy is on the fence, considering it but not sure...this article contains testimonials from straight men who love it.
Best of luck encouraging your man to let you explore his sweet, handsome ass....