How to Guide to Pegging your Man

Pegging is just like any role play in the bedroom is all about exploration, love, sharing, arousal and most of all fun. Don’t get too serious about it the first time. If you’d like a few tips for you initial venture into pegging and wearing a dildo harness we’ve put together this little guide.

As mentioned on our How to Wear a Dildo Harness page, get used to how your harness feels on you. Equip it with your favourite dildo and thrust your hips, walk around the room, bend, stretch and make any adjustments to the fitting before you use the harness for the first time. Do this in private and as you become accustomed to the mental and physical effects of wearing the dildo harness you’ll gain confidence and be prepared for the first pegging session!

You need to appear to your lover that you know what exactly how to anally penetrate him and that you’re taking control of playtime. This is particularly important if he is about to become his submissive self and is excited at the thought of you dominating him. Take a look at our pages in the Divine Domination section for some tips. Your newly acquired skills of domination and sexual power may surprise and arouse you! Relish the sensations of being in control!

Position your Lover in Readiness for your attention:

There are 2 basic positions for your “Bend Over Boyfriend” to adopt:

Bent over a supportive surface that’s just a little lower than his waist height, with his feet securely on the ground. Beds or tables are ideal and offer support if he should become weak at the knees! This position will ensure his bottom is nicely presented to you, you may even want to give him a gentle spank before you start!

Lying on his back in a “Missionary” type position. This is the most comfortable position for anal intercourse and strap on dildo play, but often the least preferred by submissive men because the sensation of vulnerability is missing. In this position he lies on the bed with a pillow to support the small of his back and his legs pulled up. You would then penetrate him from above.

Lubrication:

Any anal play is really so much better when you use a good quality lubricant. As he’s bent over waiting your attention apply a generous amount of lubricant to your silicone cock, simulate male masturbation and glide your hand up and down its shaft. Let him see what you’re doing. Tell him what you’re doing, and where the dildo is about to go.

Next apply some lubricant to his rosebud. Rub it around. To help him prepare and relax his sphincter massage a little lubricant inside him, gently and sensually push your finger in and out several times.

Penetration:

Take the shaft of your slippery silicone penis in one hand and guide its head so that it’s gently nudging at the entrance of his anus. Slowly start to push it inside him. Don’t force it, wait for his sphincter muscles to relax and accept the intrusion. As the dildo’s head enters about 25 – 50mm wait a little more, giving him time to become accustomed to the sensation. The first time it’s essential to go slowly and gently.

Thrusting:

With his bottom presented before you use it for support! Place your hands upon his hips and hold him. Now push forward with your hips in one gentle slow confident motion, until the dildo is completely inside him. Again wait a moment or two and let him get used to the sensation of being penetrated by you.

Now using your hips glide the dildo about half way out, then back in again. Continue pushing in, and pulling almost out. In and almost out. Check your lover’s body language. If he’s ready, build up a regular thrusting rhythm, perhaps going faster, deeper and with more force. As you develop your thrusting techniques it’s normally best to ensure the dildo doesn’t actually come all the way out. Bear in mind what you like when you normally have intercourse together: do you like it deep, with a regular rhythm, or would you like him to pull out completely and thrust back in again?

As your skills grow, try to develop variations: pull out completely and let him beg for more! Pull out completely and gently nudge at his entrance, not allowing the dildo to enter until you’re ready. Spank his bottom as he awaits your pleasure. Whilst fucking him with your strap on don’t forget to give his cock some attention too.

The affect on his prostate:

Pegging can’t fail to have an effect on the male prostate. As your dildo enters him it’s massaging his g-spot pleasure centre, and the sensations he feels will be those of “prostate milking” which increases arousal and gets his ejaculatory fluid flowing. His cock may start to drip and he may even ejaculate without orgasm.

Further Reading:

← Pegging – What’s it all about?

→ How to Wear a Dildo Harness – a helpful guide

→ Ideal Pegging products – dildos and harnesses

Suggested Reading:

LookBook – Male Submission – Gallery of our photos

Male Chastity – Lock Him Up – What’s it About?

Music From The 50 Shades Trilogy – What Makes Your Scene?

Female Sexual Submission

Establishing Your Authority In A Scene