Bend Over, Boyfriend!

Written by on 08/23/2013 in Sex for Couples

Pegging and anal sex for men: sex tips by Scarlett RyanEver fancied getting a taste of what it’s like on the other side? Once considered extremely taboo and rarely mentioned even in sex guides, anally penetrating your boyfriend is currently in vogue, at least if Google is to be believed, and the act has even acquired the hilarious term “BOB-ing,” with the acronym standing for “bend over boyfriend.” If you and your man are already quite adventurous, why not give it a whirl? First things first, however . . .

Part One: Have You Found His P-Spot Yet?

Some guys have a bit of a phobia about anal sex play, which is a shame because that’s the only way to find his P-spot, otherwise known as the male G-spot. If he’s adept at finding yours, then you might want to return the favor by stimulating his. All you need is some lubrication and either a clean and manicured finger or a specially designed sex toy. Don’t just go sticking your vibrator or dildo up there, not even in revenge for the time he tried the “oops, it slipped” trick . . . There are sex toys for men and couple’s sex toys specifically designed for targeted anal and prostate stimulation. Finding his P-spot is reported to give him a whole new level of pleasure he won’t have felt before, and if you couple it with an amazing hand job or oral–see previous articles for tips–then he should experience a powerful ejaculation, and be one grateful boy.

So how do you get to it? Make sure he’s relaxed and aroused; give him a massage and some foreplay, and tease him by massaging around his butt–use your tongue to flick around the opening if he’s into it–and apply plenty of water-based lubricant to your hand and his anus. Start with one finger, and go slowly. His immediate reaction might be to tense up, as he’ll feel like he needs the toilet, so stop for a minute to allow him to relax. Try giving him some enthusiastic head to keep his arousal up. When he’s relaxed a little, you’ll find his P-spot on the front wall of his ass passage, a roundish lump that will feel different in texture, often a bit bumpy like a walnut shell. When you’ve found it, massage with a “come here” motion. If you can, use two fingers. It’s much the same technique as he would use on your G-spot, but be a lot gentler. Let his reactions guide you. Press a little harder when he’s near to ejaculation; combining this with oral or with either him or you masturbating him should give him an orgasm he’ll never forget.

Part Two: Taking it Further, Without Terrifying Him!

Once he’s comfortable with anal play and you’re confident with locating his special spot, you can try a male G-spot massager designed to give him an even more intense sensation. These handy toys may look different from a female G-spot dildo in that they tend to be more ridged and curved in keeping with the contours of his ass. If he enjoys these, you might want to get a bit more experimental with butt plugs or anal beads. Although not specifically designed to target his prostate, if he turns out to be a big fan of anal he may get a lot of pleasure from these–and you can share them too. You can also progress to using a strap-on on him, and there are strap-ons specifically for the male spot. But I’d wait a while before suggesting that one. Start small, and slow.

Does he seem terrified by the whole idea? There could be a few different reasons for this; I did a quick questionnaire and got the following responses, accompanied by facial expressions ranging from a little nauseous to downright traumatized.

“It just seems unmanly. The man does the penetrating.”
“Won’t it hurt?’
“Isn’t it just for gay men?”
“I’d actually like to try it, but I’m worried she will think I’m a freak.”
“It’s an exit, not an entrance.” (This from a guy who adores giving his wife anal sex!)

Unfortunately a lot of men, no matter how liberated they are in other areas, draw a line at anything going near their ass. This is a shame because it’s usually intensely pleasurable for them due to the prostate gland mentioned above. Also, he shouldn’t expect you to want to try it if he’s going to be a baby about it himself! Don’t push him, but if he seems at all receptive, point out how pleasurable it can be for him. And no, it doesn’t make him gay. If he prefers to sleep with other men, he’s gay. If he doesn’t, he’s not. You’re not going to change his sexuality by introducing him to the joys of anal, no matter how much he likes it.

Of course, there are a lot of men who have no qualms with being anally penetrated and already actively enjoy it. These men tend to be those who enjoy being dominated by their partner in general, though not always.

Therein lies the problem for a lot of men who shy away from the idea even though they are secretly intrigued: the thought of giving up their traditional male role and being the taker in the sex act, not the receiver. For a completely hetero guy, this is probably a feeling he has never experienced, and it may be unnerving. If you can convince him to let you find his P-spot as above, he may well change his mind when he realizes how good it feels, but some men will just never be comfortable with the idea.

It is becoming more mainstream, though; a quick Google will bring up a plethora of blogs advising you how to please your man by fingering or otherwise penetrating his ass, and there’s been a rise of porn films featuring girls using strap-ons on the man, known as “bend over boyfriend” films.

How to Use a Strap-on On Your Man

How about you: would you like to be the dominant one in the bedroom for a change? If you fantasize about taking control of your man and wielding more of the power, then the ultimate way to do this is with complete role reversal: use a strap-on sex toy to do the penetrating. You both get to experience intercourse from the other’s perspective as well, which can lead to greater intimacy and understanding of each other.

So if you’ve discussed it and agreed it’s something you would both like to try, get yourselves a strap-on and give it a go. Below is a step-by-step how-to guide to get the most from strap-on play with your man.

Choose your strap-on wisely; you want it to be comfortable, but also tight enough to stop it from moving around and chafing. Go for one with an adjustable harness, and think about where it will do up; round your thighs, or would you prefer one that fits like a G-string?

Lube him up. For maximum pleasure and no pain, lubrication is essential. I wouldn’t recommend using a strap-on if your boyfriend is unused to anal play; try using fingers or male sex toys to get him used to the sensation of anal sex.

Go for a strap-on that is especially designed for male anal sex; the dildo will be curved in a way that’s designed to hit his prostate gland, also known as the male G-spot. See above for a quick guide to stimulation of this spot. Around five inches is the ideal size for the shaft; you might like the idea of penetrating him with a huge dildo, but this could cause him more pain than pleasure!

One of the best positions for butt sex is actually missionary; try it until he’s comfortable before you experiment with bending him over! This sex act is also known as “pegging.”

Start off gently, and don’t try and shove it all in at once! Clasp your hand around the head of the dildo to keep control, and ease a little way inside of him. Give his sphincter muscle time to relax and him to get used to how the dildo feels by pausing for a few moments before easing the rest of the strap-on in, bit by bit.

Finally, get into a nice comfortable rhythm and continue; listen to him and read his reactions to know when he wants it harder and is close to orgasm. Revel in your power!

To end on a cautionary note–when it comes to his butt or yours, use a toy that’s especially designed for your anus. If you use a regular vibrator or dildo it may get stuck, even traveling all the way up to your large intestine, and will make for a very embarrassing trip to the hospital. Strap-ons are fine, as of course they’re attached to you on the other end!

Believe it or not, it’s not an uncommon phenomenon. Objects reported to have been found lodged in someone’s ass, according to sexpert Tracy Cox in her book Supersex (interestingly it’s nearly always a guy), include:

  • a teacup
  • a torch
  • jars and tins
  • a pig’s tail
  • a pair of glasses
  • a grenade (?!)

The mind boggles . . .

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Scarlett Ryan

Scarlett Ryan is a thirty-two year old former porn actress, having worked for Playboy TV, Red Hot TV and Television X, among others. She now writes erotica and, as she once stated in an interview, she aims to "turn the whole world on!" Her memoir, Sex in Stilettos: My Life in Porn is available from Peaches Press on Amazon. She also practices yoga, which keeps her sane.

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