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Pegging Your Cuckold
So you have decided to 'peg' him. Perhaps as part of the humiliation you will have your boyfriend watching even assisting you.

Youíve bought yourself a strap-on (or he has presented you with one). But now you realize you aren't quite sure what to do after you put it on. This is natural reaction. After all, you've never been behind the wheel, so to speak.

Be a Take-Charge Woman
The key to success on your "first time" is to remain calm and act like you know exactly what you're doing. Guys do the same thing the first time they get into a woman's pants. Now it's your turn. Remember that you are in charge. In offering his ass to you, your boyfriend is making himself extremely vulnerable and placing an incredible amount of trust in you. You must convince your boyfriend that you are up to the challenge.

At the same time, remember that the point is for both of you to have fun. If he wants you to dominate him, get into the role and claim your full sexual power. You may find yourself surprised at how turned on you get when you allow yourself to enjoy the feeling of being in control.

Bend Him Over

Once you have your strap-on firmly in place, it's time to start the fun. The best position for the beginner is with him bent over something that is less than waist height - a table, a chair, the bed, etc. This will put his ass in the air where you can get to it, allowing for the most comfortable entry, and give him something to hang on to so you don't accidentally knock him over when his knees go weak.

Next, take some water-based lube and apply a generous amount to the head and shaft of the strap-on and to his asshole. You may even want to massage the lube into his hole with a finger or two to help relax his sphincter. If you or your boyfriend are really concerned about pain or discomfort during penetration, there are desensitizing lubes, such as Anal Eze, specifically for anal sex. If you really want to boss your boyfriend around, make him apply the lube to your dick and his ass himself.

Now that you're all lubed up, steady the dildo with one hand and place the head squarely against his pucker. Keeping a grip on the shaft of your rod, guide the head of the dildo directly into his asshole 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.

Itís the Pelvic Thrust

Place your hands on his hips and begin pushing forward steadily until the dildo is all the way in his butt. Take a couple of breaths and let his asshole 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. Keep a steady rhythm. Essentially what you are doing is massaging his prostate gland. Not only will he enjoy this, but it will also make his cock start dripping and he may even ejaculate. You can help by doing a "reach around" - reaching around to his front to play with his cock and balls while you fuck him from behind.

As youíre fucking him, pay attention to his reactions, movements and the sounds he makes. Take your cues from the intensity of his moans and groans, the speed of his breathing, and his bodyís actions. You may be afraid of hurting him, but if heís breathlessly begging you to pound him and pushing himself back onto your dick, itís time to let yourself go. Communication is important, so be sure he lets you know what he wants and tells you if he feels any discomfort.

Getting Creative

After you have gotten the hang of the basics, you can explore with different positions. Try having him lay on his back with his legs in the air or over your shoulders. Put a pillow under his butt to lift it off the bed a bit. In this position, you can kiss him, squeeze his nipples or stroke his dick. Or lay back yourself and have him get on top and ride your dick like the Pony Express.

If he really gets into being dominated, you could try spanking him first to make his ass warm and eager for your entry. You can also use additional sex toys for variety. Prep him for plowing with a butt plug, or make him wear a cock ring to keep him hard and delay his ejaculation. The possibilities are limited only by your imagination. So be bold, be creative, and be in charge of your fantasies.
Very little will reset the dynamics of a marriage faster than pushing your husband over the bed or some other piece of furniture - or better yet, using elements of bondage to ensure his compliance - and giving him a taste of what it is to be on the receiving end of a good fucking. To make sure he doesnít pull away from you, consider tying off his balls to say the foot of the bed or some other immovable object within range. Who says a side order of CBT canít be enjoyed with your pegging entree?
With our societal norms and tendency toward homophobia (especially among males) such a practice is truly humbling for the cuckold. I do advise going slowly and gently - at least at first. Whatís even worse for your boy is that this intrusion can actually stimulate him - to his utter horror. To his defense, itís not that he desires being had this way, but a physiological reaction to stimuli that he canít help. Of course, the more submissive cuckold will also respond well to the submissive expression inherent in such an experience.

This is simply one additional way to explore the dynamics of a D/s relationship within a marriage and as with many of the other aspects presented here isnít something all couples will try or even find appealing in any way - and thatís just fine.
Pegging Tips
Sample Stories
"Ahhhh, that's my boy." She murmured in my ear, pushing fingers just a bit further inside me. I felt my ass open up even more and pushed back hard. Amanda chuckled at my eagerness, stroked me a few more times and then the emptiness returned. When she moved behind me, I felt the vulnerability of the blindfold most acutely at that point. What the hell had I asked for? I felt the head of the dildo touch me, cool and smooth. She leaned in a bit and stopped. I knew she'd allow me the time I needed before the "hard and deep" commenced. That trust was such a sweet and necessary element to all this kinkiness.
I kept pushing back little by little, breathing and relaxing until the head slipped in. That feeling was always so nice; simultaneously a relief and a thrill. I felt stretched and incredibly filled...with what, I still wasn't sure, I thought to myself. I stopped wondering and got lost in the sensations as she slid gradually inside me, inch by glorious inch. As good as her fingers or a plug felt, there was just nothing like her strapĀ]on in my ass for the delicious and intense coupling I craved. Her, inside me was what made me come the hardest, interestingly enough.

Read more 'Power Play'