• How to use a strap-on on him (Pegging)

    Tracey Cox Supersex Glass Dildos

    ‘Pegging’ - women using a fake penis to penetrate their man - is becoming more and more common. And there are plenty of reasons why: it’s a power rush for both of you, and feels pretty good his end. And no, it doesn’t mean he’s secretly gay!

    Is it dodgy if he wants me to ‘peg’ him?

    As I said, wanting you to penetrate him doesn’t mean he’s gay, secretly longs to be a woman or wants you to be more dominant out of the bedroom. The appeal lies in the novelty factor (you’re inside him instead of vice versa), the fact that it’s ‘forbidden’ and that the prostate gland lies inside the rectum and gives explosive orgasms when that area is simulated.

    So lots of reasons, none remotely dodgy, why he’d want to give it a go.

    Plus it’s sexy for you as well: the experience of being ‘the boy’ is incredibly erotic, it’s a power rush and you feel naughty and edgy doing it.


    Having said all that, it's not the sort of sex treat you surprise someone with. So talk about it first together, then start preparing if he's up for it!

    Start training:

    You need to build up to anal sex with a dildo the same way you would for anal sex with a penis. It's one thing having a tongue or finger inserted anally, quite another thrusting even a small penis-size dildo inside him.

    The anus has two sphincter muscles, about a quarter of an inch apart. The 'outside' sphincter we have control over, the 'inside' sphincter is controlled by our autonomic nervous system which basically means it does what it wants, when it wants to. And it doesn't particularly like strange, unwanted things coming anywhere near it.

    If he says it's hurting when you attempt it, it's usually because this muscle has tensed around the dildo. The only way to stop this happening is to desensitise it. He can help enormously by inserting a finger inside himself every day for a few weeks - however weird that sounds, it works!

    In sessions before you're about to try using the strap-on, play gently around the outside of the anus with well-lubed fingers, then insert one finger inside, hold still until he's used to it, then thrust gently. Try inserting two fingers (cross them over) with more lube, until he's relaxed with things inside him.

    Bottoms are used to things coming out of them, not going in: you need to build up to pegging.

    Choose the dildo and harness:

    Dildos are the world's oldest sex toys, so not surprisingly there are loads to choose from. So go online and choose your equipment together. For the first time, go slim and on the small side and don't spend tons on the dildo or the harness (make sure you like it before you invest heavily). Having said that, avoid elastic harnesses and go for something made of vinyl or a strong material that has adjustable straps. (You can hold the dildo in your hand but a harness means your hands are free to stimulate other bits) The standard model has straps which go around your thighs and another around your waist. But you can also buy harnesses that attach to your thigh that fix on with Velcro.

    Dildos come in all shapes, sizes and materials and some have a pocket for you to insert a bullet vibrator inside to create extra sensation.

    The dildo is either already attached or fits into a pocket. It's a very good idea to practise wearing a strap-on before trying it out with your partner, just in case you get a fit of the giggles or feel silly. Thrusting isn't as easy as it looks and takes a bit to get the hang of it!

    Have lots of foreplay including anal play:

    Use the strap-on later on in the session rather than first thing. Make sure he's fully aroused and that you've used your fingers (and tongue if you fancy it) to ensure he's relaxed and ready for more.

    Put on the harness:

    If you're wearing it on your crotch, the straps need to be comfortable but tight enough to hold the dildo firmly in place. It needs to be pointing straight out or slightly up. If it's hanging too low, it's hard to control, and too high isn't good either. Make sure it's aligned with your pubic bone so it's at the right angle for penetration.

    Get into position:

    One word of warning on position: not all men want to try this doggy-style, as in you behind them. Some guys like lying on their back with their legs in the air, face to face in the good old missionary position. This totally freaks out some women because it's a little too feminine, but him lying on his back, with a pillow in the small or it and legs pulled up, is one of the most comfortable positions for the first time. You then enter him from on top.

    Use lots of water-based or anal lubricant:

    Apply liberally, both on the dildo and on and in his anus. If you're using silicone lube, check the label to make sure it's not going to 'eat' the dildo you're using.

    Take it very slowly:

    Insert one or two fingers before introducing the strap-on. Then hold the base of the dildo and place the head against the opening and penetrate the head only. Insert a little at a time, checking with him at each stage. Once you're all in (and you might not fully penetrate on the first try), stop and wait for him to relax around you. Get him to bear down (as though he's going to the toilet) which opens the anus.

    Be bloody careful:

    If he says 'Stop!' stop immediately. It usually means the muscles have gone into spasm. If you don't wait for them to relax before continuing, it's not just going to hurt, it's going to HURT LIKE HELL! Don't move. Just wait for him to relax and see if the pain recedes and pleasure replaces it. If not, gently and slowly withdraw completely.

    Thrust gently:

    Start thrusting only when he's relaxed around the dildo and is ready. Even then, keep it slow, gentle and shallow and be totally guided by him as to how deep, how fast and how long you thrust.

    For information on two women using a strap-on together, see Tracey's previous post on How to use a Strap-on. For more advice on warming him up for pegging and strap-on play, check out Anal Foreplay and Sex Positions from the archives.

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