Anal play involving fingers and tongue and small butt plugs and whatnot to work up to it isn't a "middle ground"?

@1: Right?

"Would that make it easier if we were both experimenting with each other's butts?"

Sure! Don't rush straight in, fergoodness'sake.

"Dude"..?

Dude, where's my strap-on!?

Where's my strap-on, dude?!

A stoner romp for the ages.

LW: Whatever you do, do not ram things up his butt. Do it slow and use loads of lube. After you've used "fingers and tongue and small butt plugs and whatnot to work up to it", as suggested @ 1.

Ramming is for experts, not beginners.

I think Dan's advice was a bit lacking on this one, it seems obvious that there is a middle ground like XiaoGui17 said @ 1. We started out with fingers and a butt plug, I bought my husband a really cute little butt plug called "The Bootie" which was a success and prepared him for bigger things. It took me quite a long time to accept the idea of fucking him, I'm ashamed to say, but back then I'd never heard of Dan Savage or GGG.
I've never heard of Broad City (don't live in the USA, who knows when we will get it) and haven't watched the video yet, though. Maybe it's highly instructive.
I'm incapable of finding it, but quite a while ago Dan wrote a response to one LW that described in great detail how to get a partner ready for anal sex, which had the side bonus of being quite a hot piece of writing. I would have thought this was a good time to respond in a similar way.

Uh what?

If the guy wants to get pegged, he's probably stuck stuff up his butt, and may have a favorite toy. Watching him and his toy would give you one place to start. Going to a sex shop together to browse might be fun and give you an idea of selection. Or google "buy strap on" and get something with good reviews. He can let you know about his width prefs, and you decide what harness might fit best and if you want a vibe included etc.

Yes you should use fingers first, way easier to get a better idea of the areas and motions he likes. Trim your nails or use gloves. Do I need to say lube?

Don't be afraid to try several positions to see what works best for the two of you. It might be less embarrassing if he's facing away... but face to face you can see what he likes better I think, it can be great feedback depending on the awkwardness level.

So it's probably a combination of reading Savage Love and being with a woman for so long, but I haven't seen pegging as a huge commitment when male partners have asked for it. I already own the (sterilizable) equipment and I like doing things my partners will enjoy.

All that being said - I think hand-held dildos are easier to control, and it's probably a good idea to figure out how your partner likes to be stimulated that way before adding the complication of controlling a strap-on that might be uncooperative at first. (They don't provide much by way of haptic feedback, so it's sometimes hard to tell how deep you're in/what angle you're moving at etc. And if you haven't strapped yourself in tightly enough it's even more difficult.)

@7 is right. If he's asking for this he's already experimented on his own and knows what he can handle. Just ask him what he wants and do it. But be careful with depth, go slow until it's in as far as it can go.

Oh. And don't forget to douche first.

@6,

I remember that anal play instruction column from a few years ago. Was a pretty entertaining read for a particularly squeamish & straight laced dude like myself.

Hasn't this been posted like three times over the past 4 years? Is Dan just posting old letters at this point?

"Where do you even go to buy stuff like that?" A sex toy shop, of course. Look for a woman-run sex shop as they are more about the toys and less about creepy guys in raincoats. The staff there are experts, they won't be fazed at all by your questions, they'll show you how to use a harness, and they'll have a variety of sizes to choose from.

Completely agree with @1: of course there is a middle ground. Start with fingers and small toys, and yes, do have him play with your bum as well. It's very helpful when you know what the person on the end of your dildo is feeling, particularly as, like @9 says, you won't be able to feel anything from the inside.

May be worth googling Dan's earlier anal sex instructions, they were exceptionally detailed.

@14: "Look for a woman-run sex shop as they are more about the toys and less about creepy guys in raincoats."

Or look for a sex shop run by gay men. There's one here in Austin, the staff were experts with discerning taste when it came to anal toys and lubes and whatnot.

Now, if I wanted a clit tickler, yeah I'd probably go to a woman-run sex shop.

Dan's column, "Ass Ed", referenced by several other posters.

http://www.thestranger.com/seattle/Savag…

Philophile, you're absolutely right, I forgot to say that my husband had already been using a dildo by himself and knew what size he could comfortably take. He'd actually bought it wanting me to use it on him but I was too freaked out about it until I knew better. At least he had some fun with it while waiting for me to get used to the idea (which luckily happened).

So has The Stranger doesn’t have a copy editor?

‘We talked about it a lot, and it's both something we have never done before.’

@20: It's the content of the letter, and while awkward, still makes sense. It's something neither of them have done before.

The first woman who ever pegged me had no idea what to do, and did what the writer asked - rammed it in. WRONG. Take your time, ease into it, use a lot of lube. My experience was pretty bad, and we never got back to it. And then we broke up.

Dude, Dan must feel like Ilana all the time. "You know, you wouldn't have written me if you didn't."

I would have at least mentioned the need for lots of foreplay and lube.

Unusually lazy and unhelpful answer by Dan.

I don't see the value in Dan posting the same anal advice on this topic every time. The advice needed for anal penetration is easy as hell to find. People write to him for entertainment, we read for entertainment. Posting about lots of lube and going slow is something we've all read 45723423 times and it's NOT entertaining anymore.