I am a regular listener of Dan Savage's podcast. I started listening at a critical time in my life when I had a strong desire to reconnect with my sexuality after a sexless marriage ended. Dan was good medicine for that. He persistently advocates the need for embracing and exploring one's kinks. That really hit home for me.
I'd been hiding my loving of pegging and dominance for too many years...as well as my erotica! So Dan was the catalyst for my own personal "coming out". (No surprise I am now a writer of erotic stories about pegging, many with FemDom overtones...Oh yeah.)
I've come a long way since then. I've explored the depths of pegging (I know, I know - but I couldn't resist the pun) and I continue to learn more about it as time goes on. There are so many questions to ask and answers to listen to...equipment to try out...and research to be done!
I still listen to Dan. He rocks. The other day a man called in who said his cock was too big for anal sex with the women he dated; scared them off. He was asking if he should just resign himself to never being able to enjoy anal because of his size...and wondered if Dan had any suggestions. Dan recommended anal play but not insertion, getting her used to being relaxed around anal play and trusting him...and that it might at some point turn into insertion...given enough time.
You men out there who are blessed with a larger than average size cock, you have probably had similar experiences...women blanching at the thought of allowing your engorged member to fill up their ass (and then some). Many years ago I recall telling one well-endowed lover that anal just wasn't in the cards...it was the price to pay for having a big cock.
I think differently nowadays. Here is my suggestion. First of all I believe that to give good anal, you need to receive it. So it stands to reason that if a man with a large cock would like to do his woman in the ass with it...he should be willing to allow her to peg him with the same size dildo. It could be something they both work up to! Actually that sounds way hot to me...probably because I am rather anally obsessed.
I can just hear the conversation...they are hot and heavy in bed and he's rubbing her butt and playing with her ass...telling her how much he wants to fuck her there. She kisses him long and deep and then pulls back and says..."Let's make a deal, Honey..."