Obviously someone who doesn’t remember Satan and Heather.
You know, if you just go on and indulge this fantasy once for him, I bet that the novelty will wear off and he’ll get bored with the whole thing within several decades.
Of course if you do this, the next time you look on his browser you’ll find it full of sites about threesomes with Swedish cheerleaders.
Thanks for the replies all. I think the course of action is to get him roaring drunk and then ask what his fantasies are and which of them he wants to try out.
Thanks for the advice on how to go about it - wouldn’t wanna be fishing in the blue if it were.
And swedish cheerleaders are fine by me!
Tikster
Vanilla has a porn site? Are you sure?
I have a very difficult time reconciling that with what she’s posted.
On topic, I’d just echo those who say: just initiate a discussion about fantasies and see where it leads. Much better than trying to intuit someone’s inner mental workings based on internet links.
[QUOTE= matt_mcl]
… he also needs to get your anus to relax.
[QUOTE]
I’m wiping away the tears as I type…
Heh, in Rhode Island, that number belongs to a plumbing company. “Hello? Yes, I need you to come over and snake my pipes…”
Keep in mind that the walls between compartments are pretty flexible. A finger in your anus can massage your G spot.
“Why yes honey, I’ve always had this fantasy of you in a vat of potato salad dressed up as cookie monster fisting an inflatable Captain Kirk doll!” Who could resist an invitation like that to throw out the weirdest thing possible? 
/Wanders off pondering why he doesn’t have a girlfriend.
See, that’s what I like about this board. So many people on it have helpful real life experience in these important matters.
Same advice you’ve already gotten, really. Lots of lube, go slow and relax. I had a… um… hangup about… uh… poo when I first did it, but you get over that pretty quickly. My cry was always “But what if there’s poo!!!” My very nifty girlfriend replied with “What if there is? You think I don’t somewhat expect that?” Heh.
I love it now and actually prefer it a lot of the time to vaginal penetration.
Ahem
I can’t believe I’m actually going to post here, but:
Yes, a nice, long, sensual massage is just the ticket. Lots of warm, scented oil applied generously to the entire body, paying special attention to the relaxation part of the massage. The oil can be used to lube both vagina and anus. It also helps if the intent to have sex is part of the entire massage package. Plan on the full massage and relaxation to take a good hour or better. Well-oiled fingers should be used to gently relax the anal muscles, perhaps with some insertion involved, and like others have said, lube, lube, lube and more lube. Scented candles and low light, and plenty of big, fluffy towels are all helpful. Once the massage is over and it has moved on to genuine foreplay, adult toys can become helpful as part of the process of relaxing and warming up. Using the toys to penetrate the backside as a prelude to the “main attraction” is highly recommended because they can relax, stimulate and assist in applying the necessary lubricants. Take it slow, and enjoy the sensations. Once you get comfortable with it, you might even find that you enjoy your boyfriend occupying one place and a toy filling the other at the same time. From my personal experience, a woman who enjoys anal stimulation, even if not outright penetration, very often enjoys the feeling of having both places filled at once, to varying degrees, depending on the woman.
All in all, if done properly and with adequate patience, it can be a very arousing and rewarding experience and can open up a whole new area of exploration and pleasure for the both of you.
(and for whoever it was that said something negative about double-penetration…from what my partners have said, it’s definitely something worth exploring - “don’t knock it until you’ve tried it!”)
Oh, my, is it getting warm in here? 
First let me congratulate you on your first OP subject matter. Excellent choice, and you inderstand that we’ll expect a followup thread regarding the, er… resolution of the anal sex issue with the bf.
My suggestion is: go up to him and say, “What do you think about fucking me in the ass?” If he didn’t already have a fantasy (which I doubt), he will make one up on the spot. As a bonus, you might fulfill a completely different fantasy that many guys share. That fantasy involves the woman getting more sexually aggressive and directing the action.
Ok, well, that’s my fantasy, but maybe it’s his too. If you won’t do it for him, think about doing it for ME, a total stranger, yet one willing to share intimate sexual fantasies with you. 
Just make sure his idea of mood music isn’t “Baby Got Back”.
Two things:
First, It seems the OP didn’t actually view the hyperlinks. Is it possible the content of that porn wasn’t about the woman getting in the butt, but rather, the guy getting it? Many are the straight men who have discovered just how fun it can be, and you’ll never look at a “Strap on Tools” truck the same way again. Maybe it’s time to try introducing some toys to your sex life and see who wants what done with it? Which leads me to my second point.
If you’re interested in finding out if you enjoy this sort of thing, you don’t really need to try it with your boyfriend first. In fact, trying it solo is a great way to learn the muscle control you’re going to need. Just drop by your local Naughty Mart where I’m sure they have a great selection of dildos ranging in size from say, “pinky finger” to “traffic cone.” They also come in various colors, shapes & RPMs, as I’m sure you’re already aware.
Look, seriously, slow down here. The fact that he has links to it suggests he’s probably aroused by it. In porn. That does not translate to wanting to do it in reality. I have fantasies about things I would never even consider trying. And he might be keeping them to himself for that reason. He may have linked it, but that doesn’t mean he wants to do it.
That said, I agree with Stonebow here. Start off on your own. Get some non-threatening sex toys out and some lube and try it out. You have muscles back there that you’re going to need to learn to relax consciously. You don’t normally think about it, so you’ll have to figure out how to work them on your own. And before he penetrates you, you might want to have some idea as to what anal stimulation is physically like.
intense giggle face needed
and what is with that traffic cone sized butt plug, does anybody actually use something that big :eek:
Goatse?
Hey there, norinew, maybe we should talk! (e-mail is in the profile )