Well I haven't personally used any of the EF floggers yet but from my experience as a first time toy you likely want to go with a flogger not a whip or single-tail my reasoning for this is it takes less skill to use a flogger and its a little less sensation for someone new to that kind of activity. As far as materials for first time floggers I generally like suede leather its soft and can provide a broad range of intensity. It really depends on your price range. Hope that helped if you have more directed questions then feel free to ask.

I'd say try one of the longer rubber floggers, one of the strap floggers or the fulfill-a-fantasy flogger.

I've been debating between suede and rubber. I'm thinking I may let him pick it out, but wanted to guide him a bit .

I like this one
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I'm new at this too and this was a great first purchase. It's short enough that I can control it, but long enough that I'm not accidentally hitting with the handle all the time.

The only problem with the rubber types is that it's going to be the same basic sensation you got from the punishment plug with just a bit more length to the tails.

Soft suede is really a good way to go since it feels different than the rubber but isn't "too much" for pretty much anyone.

The one's I'm looking at are this one link and this one link .
If we go for rubber again, it will be so we don't always have to use the plug . But the leather/suede is intriguing.
I may have to get both ...

I couldn't decide, so I did get both. Should be a fun weekend

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I started off with the Fur Lined Paddle. I'm hoping to get one of the whips next.