Well, if he thinks getting pegged by you is going to be hard on him, then his bum is going to be clenched so tight in fear that it is sure to be hard on him. If he learns that this can be an incredibly pleasurable and not-at-all-painful activity he might relax a bit, and if he knows you know how to weild a phallus safely, then he might be more open to the experience. So consider getting the Bend Over Boyfriend series (recently mentioned in our interview with Carol Queen) -- the first is more instructional, the second more tittilating -- to get you both in the know and in the mood. 

There are basically two routes to go with when it comes to the actual hardware: A harness with attachable dilleto, or a double dilleto made for female givers. While a harness like the Terra Firma provides a lot of stability and the ability to swap out different sized and shaped phalluses (according to his preference, which understandably might be extra small to begin with), it can look a bit hardcore and therefore be a bit intimidating. Even the flower-decorated Purple Penetrator can be a bit...veiny. One designed for a woman to wear internally not only looks more organic, but can also give you internal and sometimes clitoral sensation during play; however, unless you've got PC muscles of steel, you mind find it trickier to aim and keep in place. 

We'd recommending going with a new product from our favorite manufacturer, Fun Factory: their "Share" toy is made of 100% medical grade silicone and designed for women. It's harness-compatible, but you could just try borrowing a pair of his Calvin Klein boxer briefs or get your own set of tightie-whities to help stabalize the toy (pull your poker through the peepee slit)--that'll look a lot less scary than old-school studded leather straps. 

Finally, before you go fencing, you should brush up on the rules of anal play, because there are plenty--too many to name here. But we'll give you the basics: Use plenty of lube, go slowly and proceed only with his permission, aim for his navel, and, finally, while doggy style is certainly traditional, try the missionary position so he can look at your bod, you can communicate more easily, and you can manhandle his own real-life phallus. 

Have fun in the Batcave!

Em & Lo