This weeks advice column in the Seattle Weekly touches on an important dilemma that many couples have. How do you introduce something new to your partner, especially when you’re not sure how they’re going to react? In this case, the topic is male anal penetration by strap-on. As hot as this is, for some guys it’s a topic to approach with quite a lot of caution or you’ll just scare them. For example (from the column):
As I heard him coming up the stairs, I greeted him at the door all decked out like a bonerific superheroine. “C’mere, pretty boy,” I growled, pumping my hips provocatively. Playing one of the Deliverance dudes was fun! I couldn’t discern whether he was terrified, horrified, or secretly turned on, so I grabbed my store-bought junk and shook it at him. It quickly became clear that he wasn’t secretly turned on.
Here’s another example:
Edina was certain her man would be game for a little anal intrusion. After all, he liked digits up his bum; wouldn’t the next step be a dildo?
For both of these ladies, I would suggest introducing the strap-on in a much more gradual way. If you know your man likes having a finger up his butt every now and then, have a conversation with him about it. Why does he like it? What does it feel like for him? Is he happy with the level of stimulation or would he like more? This is the classic mistake that we all make – we assume because someone likes a little bit of stimulation, they’re going to like a lot of stimulation when in fact, the current amount could be perfect.
After you’ve ascertained that he would like more stimulation, get Bend Over Boyfriend and watch it together or have him watch it alone, then talk about that. If he’s never seen women in strap-ons fucking guys in the ass, he may need a little desensitizing before it’s his own ass and good, hot, porn will do that and start to form some positive associations (think Pavlov but instead of a bell and food, it’s dildos and orgasms).
Then, and I know this ruins the element of surprise: go pick out the harness and dildo together. Let him see how the staff at Babeland are excited (not scared) by the idea and let him pick out the size of dildo that seems right for him. You can both ask questions and walk out feeling comfortable.
If you’re missing the element of surprise, then you can still add a little mystery as to when you’ll whip out your new purchase and have your first night of experimentation. With one caveat: if on that night, he’s not feeling up to it, that’s OK. I’ve been turned down for butt play a lot and that’s I understand because sometimes, my ass isn’t up for it either. He’s allowed to listen to his body too.
If he’s up for it, then do a lot of warm up, use a lot of lube, talk to each other and go slowly! Chances are you’ll have him making noises like he’s never made before.
So, to recap. If you want to introduce something new to your partner I would recommend the following steps:
1. Talk about it (preferably not during sex)
2. Read about it or watch porn about it
3. Pick out any necessary equipment or get more information together
4. Try it on a night when you’re both feeling up to it
5. Recognize that sometimes practice makes perfect
Shopping Advice 
