Best Feeldoe for Beginner in Anal Play?

This valentines day my fiance and I decided we wanted to try a feeldoe. I've been wanting to try a strap on for a long time, and I love the idea of the feeldoes.

I was hoping I could get some pointers:

1) Which style stays inside the vagina the best
2) Even with a feeldoe that is supposed to stay in the vagina well, is it suggested to get a harness as well just in case?
3) Suggestions on which girth/length/toy would be the best for him since he is a beginner in anal

I have some quite large appetites and enjoy large toys on ocassion but I don't want to start him off with something that's just going to be way too much for him as a beginner.

Suggestions?

Thanks!

If he's a beginner, then I'd be inclined to say go for the smallest girth they have. Which seems to be this one:

http://www.lovehoney.co.uk/product.cfm?p=1653

I'd grab a pair of harness knickers honestly, while the toys are designed to stay put ultimately it's your muscle tone that dictates whether the toy does stay put or not and you'll likely struggle enough with using it the first few times without having to worry about holding it in too. Pegging can be harder than it looks! Something  like these would give you that bit of extra security:

http://www.lovehoney.co.uk/product.cfm?p=33781

http://www.lovehoney.co.uk/product.cfm?p=32783

If you're hesitant about the feeldoe, you could always dip your toe with a pegging strap on like this one. It would be an easier learning curve for both you giving and him recieving:

http://www.lovehoney.co.uk/product.cfm?p=28425

Or even the 'advanced' version (which is still easy for beginners and is more similar in size to the feeldoe):

http://www.lovehoney.co.uk/product.cfm?p=30701

If you're worried about starting off too fast, you could always get yourself some kegal balls and get him a beginner butt plug. That way you'd be strengthening your own inner muscles (or should I say getting used to using them to hold an object in place) while slowly introducing him to butt play. Assuming you haven't done either of those already, of course :)

Thanks for the suggestion! The feeldoe you suggested is exactly the one I was thinking might be the best choice since it's nice and small and looks like it would be rather comfortable.

Are the brief version of the harness as easy to use with a feeldoe as these:

http://www.lovehoney.com/product.cfm?p=22580

It appeared that that style would make it easy to place the feeldoe (for me), but the breifs looks like they might make it a little complicated (but easier to keep the feeldoe in place).

Thanks again!

We have been into using this type of double-ended dildo for pegging for a long time and have built up quite a collection (Feeldoe Original and Stout, Vexen Nexus, Share and Share XL plus a couple of also-rans that I forget the names of.) It's very difficult to give good advice as to which one - let's face it there can be few More personal choices than a dildo! However, a harness is a must-have. In our experience none of these work well without one (I wish the manufacturers would give up on the “strapless” tag as it just leads people to thing they are useless which they aren't - they are great for giving the wearer stimulation and feedback from their partner.

We currently favour the Share XL though it does not really fit the 'beginner' tag as the receivers end is chunky and ribbed. We like it because the wearer's bulb is bigger than the Feeldoes but it's made of a softer grade of silicone than the Feeldoe which my wife prefers. The saddle of the Share and Share XL are not ribbed (the Feeldoes are) so the Feeldoe wins on giving clit stim for the wearer but gives less g-spot stim due to the smaller bulb and bulb stem.

In the end you will perhaps end up like us - eventually buy them all to see what is best.

Should say that we found a thong style harness works better than the two-strap types for this type of dildo. A harness with lots of adjustment is needed as the ring needs to be quite low to work with the position of these dildos