I came across the following set of tips for getting a guy ready for pegging that I thought I’d post. Enjoy.
Leading up to pegging
You want to peg your boy, but you think he (or you) may not be ready. There’s no need to jump right into strap-on play. In fact, it may be counter-productive. Here are some fun preliminary steps before you strap on the old strap-on.
1. Tell him you plan to take his ass with a strap-on one day. Mention it often when you touch him there. Even if it’s a long time away, just the threat or anticipation of it will be erotic for him. Let the anticipation build. The physical act may be weeks or months away or even longer, but the mental act will start immediately.
2. Give his anus lots of attention during sex. Brush against it often. You can gauge a lot from his reaction. Whether he clenches up or jerks away, or embraces the attention with a sigh or by slightly opening his legs, or push back against your touch, will tell you a lot about his frame of mind.
3. Begin small, with a finger. Tease him a lot, just playing around the rim or by inserting the tip. Take your time. As he gets into it, gradually insert more and more of your finger until you’re sure he’s comfortable with it. When he is, increase the amount of lateral movement. Your goal is two-fold – to get him used to the movement and pressure down there, and also to begin to stretch his sphincter muscles so that he’ll be able to take something bigger. When you sense he’s comfortable (and this may or may not be the first or second time you do this), try a second finger after a while.
4. If your boy has a submissive streak, let him know precisely what you’re doing. “I told you I’m going to take your ass, boy. This is just the beginning. I’m getting you ready for something a lot bigger than just my little finger. Etc.”
5. Squigged out about hygiene? Use rubber gloves (medical ones are very thin and nice). Or, get your boy used to cleaning himself out for you. If he’s submissive, let him know you expect him to be clean inside and out before you play.
6. When you’re both pretty comfortable with this, you can always move on to toys as an intermediate step before the strap-on. Anal beads are a great first toy, and you can also use butt plugs to gradually stretch his sphincter muscles and get him used to the feeling of fullness.
7. If you boy has a submissive streak, you can also create lots of tasks for him designed to get him ready. Have him wear a butt-plug for periods when you’re not around. Have him use a dildo on himself and describe it to you. Ideally, by the time you use your strap-on, he will have already accommodated a dildo of similar size.