More and more men are becoming interested in anal pleasure and comfortable with the idea of letting their female partners take control in bed. Bend Over Boyfriend (BOB) or pegging means that a woman uses a strap-on dildo to penetrate her male partner anally. Anal penetration stimulates the prostate gland, which is sometimes called the male “G-spot.” An orgasm from prostate stimulation can be the most intense a man can have.
Some couples enjoy the taboo of the woman penetrating her male partner. Many women also enjoy the role reversal of BOB and the feeling of being in control of their man’s pleasure. Some women can even have orgasms while penetrating their partner.
If you’re interested in exploring BOB with your partner, bring it up and see how he feels about it. If he’s had anal sex with you, and you’ve enjoyed it, you have an advantage in persuading him that he would enjoy it, too. You can point out that you enjoy anal sex even though you don’t have a prostate gland, so he’s sure to enjoy it even more than you do. (That may not be altogether true, but it sounds logical.) Also, if you’ve already done some anal play with him during sex, you’re that much closer to taking things one step further.
Even if he rejects the idea out of hand, you can use your feminine wiles to change his mind. The approach I recommend is similar to the one in my post How to Make Her Want Anal Sex except tailored for the male body. You will train” him to associate anal sensations with sexual pleasure because I’m a firm believer that, once a man experiences the sensual pleasure that anal play can bring, he’ll allow you to explore the possibilities a little further. Given sufficient time and patience, he will eventually allow you to take it to the ultimate step of full anal penetration with a strap-on dildo. For some men, though, there may be an additional obstacle to overcome, which I’ll talk about later.
The best time to initiate anal play is when he is turned on and desperately wants you to keep on doing whatever you’re doing. Now when do you think that might be? That’s right – when you’re giving him head. The next time you’re sucking and licking his penis, let your finger(s) wander into his crack a little bit. Massage his perineum – the area between the scrotum and the anus.
Keep your eyes and ears open during this to gauge his response. If he moans a little louder, squirms a little bit more, or provides some other positive feedback, then go on to the next step. If he jerks away or gives you a negative reaction, don’t press the issue. Just try again the next time and hope for a more positive reaction.
If you’ve gotten your positive feedback, and are confident about proceeding, lube up a finger and slide it down into the crack of his butt and over his anus. Don’t let it linger there. Just run it right over the anus slowly and see how he responds. Again, judge his reaction to decide whether or not you should proceed.
If you get another favorable reaction, try it again and this time, let your finger linger there, and perhaps perform some light massage on the anus. Assuming you are successful, put a little lube on your finger and slowly, with circular motions, stroke the outside of his opening.
Then gradually insert your finger inside the anus. Do not move it at first. Just allow him to enjoy the sensation of fullness in the anus. Next, slowly insert the finger up to the end and make circular motions with the whole wrist, without moving the finger in and out. Try to make his experience pleasurable. The key here is to make sure that you don’t rush things.
Once your man has allowed you to penetrate him with a finger, the next step is to suggest a prostate massage. If you have to, you can stress the health benefits – especially if he’s over 30 – and emphasize how much better it will be for you, rather than a doctor, to massage his prostate. My post Prostate Massage for the Ultimate Male Orgasm tells you how to give a man a much more intense orgasm than he may have ever experienced before.
After experiencing a sensual prostate massage, it won’t take much persuading for some men to reach the conclusion that something bigger pressing against their prostate might feel even better than your fingers. However, don’t go shopping for your strap-on just yet because for many men there will be one more big obstacle to overcome: the fear that if they enjoy penetration with a penis-shaped object that it means they’re gay or that you will think they are.
Of course, the first fear only makes sense if you don’t examine it too closely. By that reasoning, a straight man shouldn’t enjoy oral sex since gay men do. Because all men have the same sexual parts, they’re able to enjoy the same sensations. It’s not what you do, but who you do it with that determines whether someone is straight or gay.
The second fear is trickier. BOB puts a man in an extremely vulnerable position, not only physically, but also psychologically. He may be afraid that if he allows you to bend him over, that you won’t think of him as a real man anymore. You have to reassure him that what happens in the bedroom stays in the bedroom.
Once your man agrees to let you take him anally, follow the advice in my post How to Bend Over Your Boyfriend and Make Him Like It to ensure that it’s a great experience for both of you. If you read some of the comments about the post, you’ll see that he may be in for the sexual experience of his life, and you may be, too. Bend Over Boyfriend is a sexual practice that comes with deep potential for personal growth and really hot sex!
My book Anal Sex Secrets is a guide to great anal sex for both anal sex beginners and for couples who are searching for new things to try. To find out more about it, click here.