I would go for the Flirt. The Little Flirt is tiny, like the size of my finger. I think you would outgrow it really quickly and it would be a waste of money. The Flirt is still not very large, and it has a tapered shape so even if you can't take the whole thing right away you can start with the tip and work up to it.
There's something really perfect about the little flirt. If you want something a little bigger but still really good for beginners, the new Lil End by Doc Johnson is great. Even though it's bigger, it's so soft that it's really super easy to take. Cheap, too.
Some beginners actually do require the small size of the Little Flirt and find the tiny first bloop on it to be a blessing. Such beginners would find the regular-sized Flirt to be too large, painful, and intimidating to start out with (even on the regular-sized Flirt's first bloop). Not that I happen to know any such beginner like that, of course . . . (*cough, cough*).
Its a tough call. do you do any anal play at all now (fingers)? and if so are you easily able to accept 1 or 2
The Flirt is 1 3/8 in diameter and the Ryder is 1 1/2 so not really a big difference. I just think Ryder is nicer because you can relax around the slim neck, you still get the OOOOH factor at the bulge but it's nice and comfy once it's in. But again that's just what I think about it, I'm sure some people wouldn't like it at all.
I got the Flirt as my first, the width isn't bad, even for a beginner. It starts out nice and small so you can slowly insert it and get used to the size increase... but I found the length to be too much (and still do). Could just be a preference thing, because my Husband also used it as a first and enjoys both the length and width, although only for short periods of time.
Which would you all recommend for a first anal plug, the Flirt or the Little Flirt?
It totally depends. Have you ever penetrated yourself before, either with fingers or other objects? If so, then I would recommend the Flirt, since it's not too difficult to work up to given the moderate diameter. However, if you've never penetrated yourself anally and don't want to use fingers, I'd recommend the Little Flirt instead.
After comparing the specs of both, I'd be inclined to agree with most people here. The Little Flirt seems like it'd only be worth it if you were really against using fingers to start out in anal play. Otherwise, you'd quickly "outgrow" and rarely use it once you've progressed to larger toys.
Start with finger play and then go for the Flirt as long as you can trust yourself (and/or your partner) to only play with the part you can comfortably take. The first "bloop" is finger sized, and then the taper is nice and gradual.
I say go with the Flirt. It really isn't that big overall, it starts out thin at the tip for insertion and the taper is really user-friendly. I've gathered a pretty decent sized pile of their plugs over time and Tantus' stuff always makes me feel even more comfortable than I'm expecting, they really design awesome toys. If you're feeling super apprehensive about anal, take baby steps and get the Little Flirt, but otherwise I think the Flirt should be just fine
I would go with the flirt. The little flirt is just too small, and you will want something bigger after a few sessions with it. Like others have said, your finger will be sufficient in getting you started, then move up to the flirt.