My Dear Lady Hannibal,

Regarding your first question - How many times a week of play is ideal? The answer is different for everyone. Ideally you would play enough times to be satisfied yourself, but not so many that you tire of it or become bored. This is entirely up to you, and there is no exact right answer.

Regarding your strap on question -- The best way to answer whether he would "go for it" or not is to bring it up outside your play time. Just ask, "How do you feel about me using a strap-on?". If he immediately responds, "No way!", then you have your answer. However, if he is hesitant, unsure or answers, "Umm, I'm not sure", then you have an opening for experimentation. Definitely try it in that case, and have it available for your next session. Don't taunt him with the idea ahead of time though if he is clearly wavering in his feelings.

When you bring it up, it would be rare for him to admit, "I'd love it!" even if he's dying to try it. You might be amazed at how eager he really is, and secretly wishes he would just say "YES!". So, if you get a middle of the road answer, then I say go for it. Just use plenty of lube.

And if he won't go for penetration, you can always beat him with it, or make him use it to pleasure you.

Enjoy and Indulge,

~~ Mistress Blaze ~~

I use one on my sub as a form of reward. He was a little shy at first but he enjoys being penetrated with it and will pretty much do whatever he can for it.

Just let him know that his safety is ur first priority and concern. Also, plan before hand a way for him to let you know that it hurts (if he does go for penetration).

Otherwise, its quite enjoyable and he may find that he likes it a lot.

My boy toy loves anal penetration! He prefers a strap-on but I will tease him with other penetration for my satisfaction! I agree with Mistress Blaze, if he is a little unsure try rubbing him around the area. If he enjoys that then you can slowly work your way in. If he enjoys that then you could try stimulating the prostate, could make him cum!
I have to admit I get turned on by penetrating my boy toy, in all ways!

Also, try using a lubricant. It helps a lot. :)

---
Mistrezz Samantha