As far as my experiences go, both on the giving and receiving end, vibrating plugs are kind-of "meh". it's a totally personal choice, and if she's not worn a plug before, I'd have her try both before the session starts. Personally, if im planning to spank (or be spanked) with a plug in place, my clients (and myself) prefer non-vibrating plugs.
If I were her, I'd prefer two separate toys; one static butt plug (non-vibrating), and either a dildo or a vibrator in use (not both though, too much). I love the idea of making spanking=orgasm, so a vibrating toy on my clit would put my mind where it needs to be. You could also plug her butt, and make her play with herself while you spank her. "force" her to orgasm during the spanking. Relate that pain to pleasure. This is personally what I would do, and what I have done to numerous male and female clients alike. It's a really fun way to play. I hope you have a great time together!She does like her ass played with (and eaten out), but greek is very rare (We've done it once in the year that we've been seeing each other regularly), so, I am thinking of putting a butt plug in for the spanking. Probably small. Maybe vibrating. Maybe a double penetrating toy.
Thoughts? Do you like a butt plug for spankings? Is vibration good, or is it distracting? Should I give her a choice, or do the domination thing. (obviously, safe word trumps all).
If you were her, how would you prefer the scenario to go?
I'm pretty similar in that I'm not into Greek - well, receiving, anyway- but like to play with plugs once in a while. They're a lot of fun while being spanked; the two sensations amplify each other wonderfully.
If you want to play devious, a game I like is to put one in that you know will be too small. Have her clench it in while you're spanking her, and if (when) it pops out, punish her accordingly!
(If you want to get *really* devious, try figging and caning at the same time 
Vibration is great for relaxing the muscles, especially if you choose a plug that may be a bit bigger and more of a challenge to get in. Of course, everyone is different in what sensations they prefer. She may find it overstimulating. The only way to find out is to try everything!
I would suggest alluding to your plans before you meet so that she can veto if she so chooses. If she's excited by the idea, that'll leave you in the clear to assert your domliness, while of course respecting safewords.
For beginners, I highly suggest the pink pop plugs by Doc Johnson. The small is VERY small, so I'd suggest checking them out in person to avoid size discrepancies. They're cute and really well shaped for your purposes- they don't vibrate but have a ring at the end that you can stick a bullet vibe into if you want. Many of the nicer sex toy stores in NYC stock them.
Hope this was helpful, and have fun!
Appreciate the advice. Will definitely report back with results.
As far as my experiences go, both on the giving and receiving end, vibrating plugs are kind-of "meh". it's a totally personal choice, and if she's not worn a plug before, I'd have her try both before the session starts. Personally, if im planning to spank (or be spanked) with a plug in place, my clients (and myself) prefer non-vibrating plugs.
If I were her, I'd prefer two separate toys; one static butt plug (non-vibrating), and either a dildo or a vibrator in use (not both though, too much). I love the idea of making spanking=orgasm, so a vibrating toy on my clit would put my mind where it needs to be. You could also plug her butt, and make her play with herself while you spank her. "force" her to orgasm during the spanking. Relate that pain to pleasure.
This is personally what I would do, and what I have done to numerous male and female clients alike. It's a really fun way to play.
I hope you have a great time together!
make that little plug out of ginger...really spice up that spanking!!
K