About Me
I came to the U.S. at age of 12 with my mother. We settled in sunny Florida, which was quite a contrast to Minsk. I have always been fascinated by sex and relationships. Sex Secrets is where I share sex advice, experiences, news, and sometimes a little humor. If you have a question about sex that you prefer not to post in the comments, you can email me at svetlanaivano(at)yahoo.com.
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How to Bend Over Your Boyfriend and Make Him Like It

While it still remains taboo in some circles, heterosexual anal sex seems to be gaining in popularity, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. These days more and more men are becoming interested in anal pleasure and comfortable with the idea of letting their female partners take control in bed.

If you’ve decided to make your boyfriend’s or husband’s strap-on fantasies come true, you need to get the right equipment: a sturdy strap-on dildo and a reliable harness to hold it in place. When starting out, it’s best to choose a dildo on the smaller side, for comfort’s sake. A dildo of 5 to 6 inches in length and 1 to 1.5 inches in diameter should be an adequate size for your first strap-on. Choose a dildo that has a flange at the base that will secure it in a harness, and buy a sturdy harness with adjustable straps, preferably one of leather, vinyl, or other strong material.

Some dildos have an upward curve or special shape designed to stimulate the prostate. The prostate gland is located between the wall of the rectum and the bladder and is about the size of a walnut. It is the male equivalent of a woman’s G-spot, and stimulating it can greatly increase the intensity of the man’s orgasm, and sometimes the force or quantity of his ejaculation. While prostate stimulation can be achieved with a standard dildo, having the angle built in makes it that much easier to hit your man’s hot spot.

Once you have your strap-on firmly in place, apply a generous amount of water-based lubricant to the head and shaft of the dildo and to his anus. You may even want to massage the lube into his hole with a finger or two to help relax his sphincter. If you really want to dominate your boyfriend, make him apply the lube to your dildo and his anus himself.

Once you’re all lubed up, steady the dildo with one hand and place the head squarely against his anus. The most comfortable position for anal sex is with him lying face up with a pillow under the small of his back and his legs pulled up. You then enter him from on top, in a missionary-style position. In this position, you can kiss him, squeeze his nipples or stroke his penis. However, many couples like having the man bend over something that is less than waist height – a table, a chair, the bed, etc. – or take it doggy-style because these are more submissive postures.

Keeping a grip on the shaft of your dildo, guide the head directly into his anus and gently push it inside him. Instruct him to bear down as if going to the bathroom while you do this, to open up his sphincter muscles. Once the head of the dildo disappears (or the dildo enters into him about an inch or two), pause and let him get used to the feeling of having something up there. Then place your hands on his hips and begin pushing forward steadily until the dildo is all the way in. Take a couple of breaths and let his sphincter adjust and relax. Pull part way out slowly and push back in. Pull out, push in. Continue doing this, increasing your speed and force as you go.

Essentially what you are doing is massaging his prostate gland. Not only will he enjoy this, but it will also make his penis start dripping, and he may even ejaculate without direct penile stimulation. You can increase the stimulation by exerting pressure on the dildo in the direction of the prostate so that the shaft rubs more firmly against it. Also, concentrating your thrusting motions in short, rapid movements will provide more stimulation against that area.

Keep a steady rhythm going, but pay attention to the intensity of his moans and groans, the speed of his breathing, and his body’s actions. Communication is important, so be sure he lets you know what he wants and tells you if he feels any discomfort. Though you may be afraid of hurting him, if he’s begging you to pound him and pushing himself back onto your dildo, it’s a sign to let yourself go. You may find yourself surprised at how turned on you get when you allow yourself to enjoy the feeling of being in control.

Beyond male anal pleasure, there is a lot to explore in the area of role reversals with BOB. It’s a chance to explore the ways you feel – masculine and feminine, bottom and top – and a chance to relate to your partner in a completely different way. Bend Over Boyfriend is a sexual practice that comes with deep potential for personal growth and really hot sex!

If you’re a woman who is turned on by the idea of pegging your man, but he’s not so eager, try the tips in my post Bend Over Boyfriend: How to Make HIM Want Anal Sex. You may be shopping together for a strap-on sooner than you think!

The Feeldoe is an amazing sex toy that combines the excitement of strap-on sex and the pleasures of mutual penetration without the hassles of a harness! The bulb end of the dildo is held inside the vagina by contracting the vaginal muscles. The ridged portion stimulates your clitoris as the shaft penetrates your partner at just the right angle! To find out more, click here!

54 Responses to How to Bend Over Your Boyfriend and Make Him Like It

  • masok says:

    For those who may have not tried this be assured many men really desire it and it is not because they have homosexual tendencies or are secretly gay. It is simply that the feelnig is fantastic. Also the relinquishment of control to your female partner is very empowering for them. Above the intensity of male orgasm is much ehnhanced and the extent of ejaculation often much more than in standard sexul acts – try it !!

  • Toni says:

    For me there was a strange feeling of real power when I looked down for the first time and saw a nice cock jutting out from between my legs. I surprised my man by making him suck my “cock” before I fucked him. It was so hot. He was also surprised when he climaxed with touching himself. He said that the sight of me fucking him, the feelings in his ass, and watching my tits bounce were all too much for him and he just came and came. I climaxed also from the power thing and the stimulation of the base of the dildo on my clit when I pounded into him. I totally recommend this if he has any interest in anal play at all.

  • This is an excellent article. One of the things I remember when i tried this with an ex was how I didn’t really have a good way to tell what was going on “down there.” Without the sense of touch to tell me how hard or soft I was doing things, I started out really nervous about hurting him. A step by step set of instructions like the ones above would have helped. Of course, with his direction I got into it eventually and we had a GREAT time.

  • Svetlana Ivanova says:

    A good rule of thumb is to go slow and easy until he lets you know (one way or another) that he wants you to go hard and fast.

  • Marcello says:

    Excellent Post.

    I find that starting with some fingering is a great way to get things going, and when she inserts her finger in your anus you will feel a sense of connection to her that you could have never imagined until you do this.

    My favorite position is that modified missionary position with the pillow, but I love to finish lying on my stomach, with her pressing her body against my back, incredible!

  • Svetlana Ivanova says:

    I agree that “fingers first” is a good idea. In fact, all of the steps in my post 10 Steps to Great First-Time Anal Sex apply to Bend Over Boyfriend. I would further recommend doing a prostate massage before moving on to inserting a dildo to get your man comfortable with anal penetration.

  • Mr Kink says:

    Nice article, and I’m with you 100%. As a straight married couple, strap-on play has been a part of playtime for a few years. There is a freaky feeling when Mrs Kink orgasms while taking me… quite the role reversal. I also think that she’s surprised every time I “beg” for more, by moving backwards into her as you accurately describe. Thumbs up from us. =)

  • Svetlana Ivanova says:

    “Bend Over Boyfriend” is sure to bring out some surprising feelings and sensations in both partners.

  • kruiza says:

    This is great we where doing it for years and it did not have a name. My wife felt so empowered when she began to make love to me and it made our relationship even more equal and fun

  • It’s really too bad that so many men still think it’s ‘gay’ to receive any sort of anal play from their girlfriends/wives. If you haven’t tried it you should, after that you can decide if you’re into it or not.

    For women, using a strap-on dildo on their partner may not be a turn on at all, they may even be completely turned off by the idea.

    It such a good article and I wish that more men would read it and for that matter, more women, so they could bring up the concept to their male counterparts.

  • mrs.all for anal play says:

    my husband and i just read this article and decided to try it. we have been trying to heat up the bedroom for sometime now do to the fact that we have 2 young children and its hard to find anytime for eachother.
    it was so empowering and amazing to watch him scream and climax without any penis stimulation was amazing and made me climax. i love having the power and making him beg for me! the movies are also good and you can find many helpful hints about how to properly penetrate your partners booty. i love it! and it has made us so much closer and it’s just amazing! get past the taboo strap one on you would be amazed at the feeling it brings to you.

  • Svetlana Ivanova says:

    I’m glad to hear that you had such a great time experimenting with anal play.. A lot of men have no idea that they can climax without penile stimulation, but they can, and, as you say, we women can get our own enjoyment from penetrating our partners.

  • Kelli Kanyon says:

    I started anal play with my hubby many years ago and worked him up slowly in size. He can now take fisting rather easy and loves it. Heheheheh and the baseball bat is “not really that big feeling becuz it is so smooth” <– those are HIS words :)


  • mike says:

    The first time I put a finger up ther. It was a bit pain full. But in the shower relaxed, I did it again, boy what a rush. I then asked my wife, who was more than happy to do it. She had wanted to but was unsure of my reaction. Well at least once a week I get pegged and boy do I look forward to it. I believe tonight is the night. :)

  • Svetlana Ivanova says:

    I’ll bet your wife looks forward to it, too.

  • Mitch says:

    my girlfriend and i are really into this. we’re at the point where shes now using a dildo bigger than what i’m packing lol! we’ve started playing out fantasies, i love dressing up in those sexy outfits and i’ve got my own boobs too, she loves it. almost every night its i’ll do u if u peg me. some people may think its weird but we get so much pleasure out of it

  • Svetlana Ivanova says:

    Glad to hear you’re both having fun. The two of you are really exploring the role reversal aspect of Bend Over Boyfriend.

  • Mitch says:

    We’re definately enjoying it, tho i know my g/f would never dress up like a bloke. Shes taking more and more control now and its now to the point where nearly every time we’re in bed i’m dressed up and shes doing me

  • Bill says:

    WOW, Wife just bought a strap on, I was a bit timid about it, but OMG what an Orgasm we both had!!

  • Svetlana Ivanova says:

    Amazing, isn’t it, Bill? Readers, if you haven’t tried this yet, don’t waste any more time. Bend Over Boyfriend can make you reconsider everything you thought you knew about sex.

  • Jaime says:

    my gf at the time told me that she wanted to fuck me with a strap-on. we bought a realistic dildo, a harness, and the dvd bend over boyfriend. we watched the video first then she grabed the toy and went into the restroom to put it on. when she came out, iwas suprised on how sexy she looked with it on. she had me give her a bj before she took me. wow, what a rush. i recomend guys to try this….

  • Svetlana Ivanova says:

    Watching the Bend Over Boyfriend video together beforehand is a good idea.

  • Brian says:

    I would love to see your take on an article titled “How to get your Girlfriend to Bend you over” I’m having some trouble barking up that tree. We’ve talked about it but she gets weirded out.

  • Svetlana Ivanova says:

    Interesting. I didn’t need any persuading, but I’ll talk to some girlfriends and get their feedback.

  • Brian says:

    Awesome : ) By the way love your site!

  • Svetlana Ivanova says:

    You must not have read this post.

  • Jim says:

    I love being bent over, but she is not into it. Help. Any suggestions on getting her to want to take control and strap it on again?

  • Svetlana Ivanova says:

    Again? What led her to try it in the first place? Try to re-create those circumstances.

  • Steven says:

    My former wife started this by wanting to use her finger and make me have an orgasm. After that we tried the strap on and she liked doing it so much that she would get wet and become so close to orgasm that all I had to do was touch her and she would come. We ended up having anal night where we both gave and received twice a month and gradually it gravitated to once a week. The other nights were for regular sex. We tried different positions with her from back, me on my back to me on my stomach with her on top. As soon as we were done than we would reverse roles and she would have an extreme anal organism with me on top and her fingers on her clitoris. Neither of us knew that anal sex would feel so good.

    This was a nice variation and livened up our love life to say the least. It opened up my horizons on what a man and woman can do together and I look forward to this again with a new girlfriend.

  • Svetlana Ivanova says:

    It’s great that you and your ex-wife experienced how great anal sex can be for both men and women. I hope you find a new girlfriend who is as open to experimentation as your former wife was.

  • larry says:

    Me and my wife always had anal sex me being in control ..But after I found svetlana sight & she looked at she wanted to try it..I actuly like getting pegged by my wife she has fun with it …We’ve been married for oh most 15 years now… This feel like a honey moon all over…She says I’m going to get tonight finger first…THANKS SVETLANA …

  • danny says:

    my wife asked me this morning to bend over .she said since she has latly she said it was my turn…I love my WIFE….

  • Svetlana Ivanova says:

    Obviously, she has made you like it :).

  • Ralphie says:

    My wife is willing to fulfill me… tomorrow night! Yes!

  • Ralphie says:

    I’m male with a strong feminine side, which I just admitted to my wife. She says she loves it but does not have a male side to her… will that come out once she “pegs” mw or continues to do it? I want the role reversal to be mutual.
    Also, on dress up, how do I get her to agree to let me into he clothes so she can fuck me like I think she really wants to…?

  • Svetlana Ivanova says:

    Simply assuming the penetrative role during sex will bring out your wife’s “male side” to some extent because it’s so different from lying back and “taking it.” As far as enhancing the role playing, just present it as that – playing roles. You can also bargain with her by asking her to play the role in your fantasy and promise to play a role in one of hers.

  • Svetlana Ivanova says:

    I think both you and your wife are going to enjoy this :).

  • Ralphie says:

    Thank you for your kind response. If you would be interested in my feedback I will share my experience(s) with you and will have more questions, I’m certain. —R

    PS— it arrived today…

  • Svetlana Ivanova says:

    Absolutely share your experiences. I know I am always interested in hearing how a male feels “taking it,” and also how a woman feels about “giving it.”

  • Ralphie says:

    Svetlana: Last night was magic. This was the first time for the both of us so as imagined it was “exciting” and a bit awkward in getting the harness and dildo attached correctly. We used a Spareparts Joque harness with a Nexus Sr dildo. First we bathed together and discussed the role playing. I have an amazingly open-minded woman and wife. Afterwards, she dressed me in her nightgown and I had her wear one of my shirts. We helped each other with the harness. She especially like the “fit” in her and it did stimulate her juices, she said. I knelt in front of her as she has me many times and orally took the dildo in my mouth. The key for the man is to take it slowly… the head of the dildo goes in easily then there is a stopping point. I just relaxed and asked her to take (at first) slow pulsing movements. Quickly I relaxed and was able to accept the whole thing. Amazing feeling! And, she didn’t want to stop, nor did I. I imagine we spent more than 15 minutes with her fucking me — on top of me, me on top of her (which I liked the best) and bent over on the side of the bed. I ejaculated like I hadn’t since I was a young man. Life is good. Thanks for your interest and this won’t be the last time you’ll hear from me. Questions? From others? Send them my way and I’ll try to help from my perspective. —R

  • Svetlana Ivanova says:

    A little awkwardness at first is natural. I told you pegging would bring out your wife’s “male side” (if you want to call it that), didn’t I? I’m glad the two of you had fun. That’s what it’s all about.

  • danny says:

    I’m wanting my wife to realy give it to me….Like I’m wanting her to ram it when I take it….I’ve orally took it..caught of guard..Now if I can get her to get wild ..Any sugestions……

  • Svetlana Ivanova says:

    Tell her what you want. She may be wanting to do it the same way, but she won’t know that you want it too until you tell her.

  • Chad says:

    I love being pegged by my wife. I aslo like oral pegging (sucking my wifes strap-on) but she is not crazy abiout it.. any suggestions? She is so hot when the is strapped up and sucking the dildo makes me crazy horney…

  • Svetlana Ivanova says:

    My only suggestion is to tell her what you just told me :).

  • WD says:

    I so want to be taken by my wife wearing a strap-on dildo. We’ve been married ten years and she’s really good to me with anal licking and fingering (she likes me to do her sometimes, but I am crazy about being on the receiving end!). So far, she has said no to toys but I’m still hoping! The sexiest thing I can imagine is a man being bent over by a woman who wants to play with his ass. I crave being in a position where she can see me completely exposed and vulnerable. Being penetrated makes me feel accepted, taken, and loved. And physically, it is beyond pleasurable. I love love love love it!

  • WD says:

    A few more thoughts:

    Being taken by a woman wearing a strap-on dildo is my fantasy and fondest sexual desire. Like I said before, I am still a virgin like that, though, because my wife has a total aversion to sex toys. Fortunately though she is as attracted to my bottom as to my penis so she gives me plenty of good loving with her mouth (analingus) and well-lubricated fingers. I have always taken pleasure in being anally stimulated and penetrated, either by myself or by women. It is incredibly pleasurable, both physically and emotionally. I simply must have it to be happy and sexually gratified.

    I want to say a couple of things that the article doesn’t stress. First, about the process of anal penetration: it goes a whole lot better for both partners if the receiver has recently had a bowel movement and a few enemas to rinse out the rectum. Just flush out a few times until the water comes out clear and there will be no mess or embarrassment. I also like how it relaxes the sphincter muscles and starts stimulating the prostate, arousing my bottom and making me feel receptive.

    Second, foreplay is usually called for. Most times the receiver doesn’t want a dildo inserted right away, just like most women don’t want to go straight to intercourse. Besides all the kissing and hugging and so on, you want to prepare the guy’s anus. Analingus is wonderful. But anal fingering is essential, with lots of lubricant. Tease him and have a lot of sexy talk as you slowly insert one finger and eventually two or maybe more. Make circular movements to relax his anus and when you have two fingers inside spread them apart. Using a dildo in your hand is good before you move on to the strap-on. Start with a slender shaft the first time, so you can both learn your way.

    My fantasy is being taken from behind, doggie-style, with me on my knees and face down as the woman presses the tip of her strap-on dildo to my anus. That’s how my wife and I usually play. The feeling of surrender and vulnerability is exquisite. It reinforces the role reversal aspect, which I love.

    Female-on-male anal is to this decade what oral sex was to the 1970s–it’s entering the mainstream. Stereotypes and hangups are falling away as both sexes realize how good it is. It may not be for everyone, but those who like the idea should go for it

  • Violet Ivy says:

    I agree…oral sex wasn’t around in the time of our parents. Anal sex on guys is now the flavor of the month as guys are getting over their homophobic concerns and discovering the pleasure this orifice can give them. Bring it on I say!!
    I’ve had literally hundreds of guys ask me to take their anal virginity. And they love it. Once it’s done gently with lots of lube they can’t get enough.
    Violet Ivy
    Lucky Girl – How I Survived the Sex Industry

  • charles says:

    After asking my wife to have anal sex, she replied “if you let me do u with a strap on, we can talk about u doing me” while she may have been joking, I would actually love to try that, not just because it means she might let me give her anal, but I just get very turned on by the idea of being pegged, do u have any suggestions how to seriously bring it uo as something to do?

  • Svetlana Ivanova says:

    She gave you your opening. Ask her if she was joking..

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