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!
If you’re like many people, you’ve had a satisfying sex life, but deep down you know there’s something missing, something you still yearn for. You’re looking for new heights of sexual satisfaction. Don’t let another night pass without experiencing deep sexual bliss. Make today the day you take your lovemaking to unimagined levels of fulfillment. To learn Tantra sex tips that work, click here.
Similar Posts:
- The Bend Over Boyfriend Test
- A Couple's Guide to Male Anal Pleasure
- Bend Over Boyfriend: How to Make HIM Want Anal Sex
- Why Do Some Couples Enjoy Bend Over Boyfriend?
- Anal Sex for Beginners
Tags: bend over boyfriend, pegging, strap-on sex
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. My sexual history and preferences are detailed in my post 
February 16th, 2008 at 6:34 am
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 !!
February 16th, 2008 at 8:17 am
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.
February 18th, 2008 at 4:24 pm
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.
February 18th, 2008 at 4:36 pm
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.
February 20th, 2008 at 3:18 pm
[...] a recent post, the Sex Secrets blog tells us girls how to properly give our fellas the ass fucking they so [...]
February 23rd, 2008 at 5:35 pm
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!
February 23rd, 2008 at 5:41 pm
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.
February 26th, 2008 at 1:04 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 3:17 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 6:04 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 8:34 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 9:53 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 11:36 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 11:56 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 7:03 pm
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 9:15 pm
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 26th, 2008 at 10:43 pm
[...] Monique Alexander, Nadia Styles & Sunny LeoneSex WorkCatalina loves Couples (D/s)Sex AdviceHow to Bend Over Your Boyfriend and Make Him Like ItThe Ultimate Sex Position?Erotic Writing and ExperiencesAfter the gaurd 2Blue AirThe Cam Lover [...]
February 27th, 2008 at 2:36 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 27th, 2008 at 8:10 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
February 27th, 2008 at 5:07 pm
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
March 10th, 2008 at 11:14 pm
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. =)
March 11th, 2008 at 5:18 am
“Bend Over Boyfriend” is sure to bring out some surprising feelings and sensations in both partners.
March 23rd, 2008 at 2:02 am
[...] psychological, and spiritual experience. Here’s how some male readers responded to my post Bend Over Boyfriend and Make Him Like It: For those who may have not tried this be assured many men really desire it and it is not because [...]
March 27th, 2008 at 7:38 am
[...] a reader asks for advice on how to talk to a reluctant partner about the issue of strap-ons and Bend Over Boyfriend or pegging. Here is one response: Well, I can’t speak from personal experience as my wife was [...]
May 16th, 2008 at 6:20 pm
[...] Asian girls have nothing on me. I admire, support, and love my man – as long as he’s willing to bend over. [...]
May 26th, 2008 at 3:12 am
[...] Advice How to Bend Over Your Boyfriend and Make Him Like It The Ultimate Sex [...]
May 31st, 2008 at 9:20 am
[...] 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, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. If you have never tried (or even heard of) this sexual practice, read my tutorial How to Bend Over Your Boyfriend and Make Him Like It. [...]
May 31st, 2008 at 9:23 am
[...] 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, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. If you have never tried (or even heard of) this sexual practice, read my tutorial How to Bend Over Your Boyfriend and Make Him Like It. [...]
May 31st, 2008 at 9:24 am
[...] 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, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. If you have never tried (or even heard of) this sexual practice, read my tutorial How to Bend Over Your Boyfriend and Make Him Like It. [...]
June 14th, 2008 at 3:16 am
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
August 18th, 2008 at 3:45 pm
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.
September 7th, 2008 at 2:08 pm
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.
September 8th, 2008 at 8:09 am
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.
September 14th, 2008 at 4:50 am
[...] 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 [...]
September 16th, 2008 at 9:39 pm
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 :)
kelli
September 20th, 2008 at 7:16 am
[...] or Bend Over Boyfriend is my new favorite sex [...]
October 5th, 2008 at 12:05 pm
[...] How to Bend Over Your Boyfriend and Make Him Like It 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. [...]
October 23rd, 2008 at 7:45 am
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. :)
October 23rd, 2008 at 12:22 pm
I’ll bet your wife looks forward to it, too.
November 7th, 2008 at 8:29 am
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
November 7th, 2008 at 4:10 pm
Glad to hear you’re both having fun. The two of you are really exploring the role reversal aspect of Bend Over Boyfriend.
November 8th, 2008 at 2:44 am
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
December 3rd, 2008 at 8:42 am
WOW, Wife just bought a strap on, I was a bit timid about it, but OMG what an Orgasm we both had!!
December 3rd, 2008 at 9:22 am
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.
January 13th, 2009 at 12:37 pm
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….
January 14th, 2009 at 5:49 am
Watching the Bend Over Boyfriend video together beforehand is a good idea.
January 21st, 2009 at 6:01 pm
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.
January 21st, 2009 at 8:30 pm
Interesting. I didn’t need any persuading, but I’ll talk to some girlfriends and get their feedback.
January 22nd, 2009 at 6:35 pm
Awesome : ) By the way love your site!
February 17th, 2009 at 6:26 pm
[...] spell to break up a relationship has over 400 comments (far more than my most commented post How to Bend Over Your Boyfriend and Make Him Like It), so there must be a lot of people interested in this topic. As with anything, your mileage may [...]
February 20th, 2009 at 9:35 am
You must not have read this post.
March 11th, 2009 at 7:00 am
[...] Posted on March 11, 2009 by Svetlana Ivanova Anonymous at AlterNet explains why he agreed to be a bend-over boyfriend. His first time didn’t go so well, but the second… The first time my girlfriend fucked [...]
June 30th, 2009 at 4:06 pm
[...] 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, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. If you have never tried (or even heard of) this sexual practice, read my tutorial How to Bend Over Your Boyfriend and Make Him Like It. [...]
July 1st, 2009 at 7:23 am
[...] psychological, and spiritual experience. Here’s how some male readers responded to my post How to Bend Over Your Boyfriend and Make Him Like It: For those who may have not tried this be assured many men really desire it and it is not because [...]
July 5th, 2009 at 1:49 pm
[...] exploring male penetration by the female partner with a strap-on dildo, a sexual practice known as Bend Over Boyfriend or [...]
July 6th, 2009 at 7:35 am
[...] How to Bend Over Your Boyfriend and Make Him Like It 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. [...]
August 2nd, 2009 at 2:29 pm
[...] a reader asks for advice on how to talk to a reluctant partner about the issue of strap-ons and Bend Over Boyfriend or pegging. Here is one response: Well, I can’t speak from personal experience as my wife was [...]
August 2nd, 2009 at 4:01 pm
[...] have nothing on me. I admire, support, and love my man – as long as he’s willing to bend over. Share and [...]
September 14th, 2009 at 5:52 am
[...] or Bend Over Boyfriend is my new favorite sex [...]
December 26th, 2009 at 5:54 pm
[...] 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 [...]
April 23rd, 2010 at 5:03 am
[...] Anal Sex Which Anal Sex Positions Are Best for Beginners? 5 Advanced Deep Throat Techniques How to Bend Over Your Boyfriend and Make Him Like It How to Make Her Want Anal Sex The 3 Best Positions for MFM Threesomes 100 Things about Me Sexually [...]
July 18th, 2010 at 8:04 pm
[...] 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, and some couples are even exploring male anal penetration by the female partner, a sexual practice known as Bend Over Boyfriend (BOB) or pegging. If you have never tried (or even heard of) this sexual practice, read my tutorial How to Bend Over Your Boyfriend and Make Him Like It. [...]
December 28th, 2010 at 7:20 pm
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?
December 29th, 2010 at 9:47 am
Again? What led her to try it in the first place? Try to re-create those circumstances.
March 27th, 2011 at 4:57 pm
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.
March 27th, 2011 at 5:30 pm
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.
September 7th, 2011 at 6:06 pm
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 …
October 31st, 2011 at 4:03 pm
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….
October 31st, 2011 at 4:20 pm
Obviously, she has made you like it :).
December 13th, 2011 at 10:50 pm
My wife is willing to fulfill me… tomorrow night! Yes!
December 13th, 2011 at 11:00 pm
Svetlana,
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…?
December 14th, 2011 at 9:31 am
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.
December 14th, 2011 at 9:32 am
I think both you and your wife are going to enjoy this :).
December 14th, 2011 at 4:47 pm
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…
December 14th, 2011 at 6:16 pm
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.”
December 15th, 2011 at 7:39 am
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
December 15th, 2011 at 9:41 am
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.
December 15th, 2011 at 8:04 pm
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……
December 16th, 2011 at 7:35 pm
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.
April 2nd, 2012 at 8:54 pm
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…
April 3rd, 2012 at 4:01 am
My only suggestion is to tell her what you just told me :).