Really really screwed up hypothetical

[Darth Wong]

No, I would not take the offer. One beautiful woman is enough for me, and I'm quite happy living in civilization.

As for the pain factor that others have alluded to, it would probably be exceedingly painful. First of all, a 9" strap-on is a huge object. Second, you will almost certainly tense up and clench due to reflex, because unless you're Einy, you're not used to the feeling of objects going in the wrong way. That clenching will make it vastly more painful.

Well, how does your wife feel about Anal Sex?

My dick is not a 9" piece of rubber.

[Einhander Sn0m4n]

No, I would not take the offer. One beautiful woman is enough for me, and I'm quite happy living in civilization.

As for the pain factor that others have alluded to, it would probably be exceedingly painful. First of all, a 9" strap-on is a huge object. Second, you will almost certainly tense up and clench due to reflex, because unless you're Einy, you're not used to the feeling of objects going in the wrong way. That clenching will make it vastly more painful.

Well, how does your wife feel about Anal Sex?

My dick is not a 9" piece of rubber.

In other words it's just the Right Size then? Yes, there is a point at which a dick can be correctly described as 'too big'. I define that as when even the horniest of guys (or girls) will think twice before taking it up their ass. And yes, I've had a couple guys plainly tell me 'No, let's suck each other off instead!'

[Darth Wong]

It is also noteworthy that a dick has some "give" to it that a piece of rubber or plastic does not. That's why women say that a dildo hurts a lot more than a real penis of the same size. It's also why pornstars rarely take big dildoes up their asses (seriously, watch some porn; only the most hardcore performers will take a big one up the ass). Even Briana Banks, no stranger to hardcore penetrations, says she doesn't like the feeling of dildoes up her ass (for those who don't know Briana Banks, let's just say her ass has had more than its share of visitors over the years).