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Oh, I forgot to ask if the small Plug of Lust should be easier to use than the Tantus Little Flirt, Tantus Small Ripple, and FunFactory Bootie! Any other suggestions would be most appreciated, too.
SS, I really love the Plug of Lust, I found it easier to use than even the "beginner" Crystal Cote silicone plug. (The Crystal Cote was just too pointy and hard when we were first experimenting with anal play, although before we got the Plug Der Lust we used it occasionally.)
I found a couple of things really help anal play progress. My Man "conditioned" me, similarly to when he taught me how to have PIV sex, decades earlier. He started with gentle fingering, no toys, just his hand and fingers lightly touching and eventually probing, all the while making sure I was happy and comfortable and eventually really aroused. This probably took a couple of weeks of just touching with minimal penetration. Then he started penetrating, little by little, until we tried the Crystal Cote....and I hated it.
I ended up being able to take his penis before any toy, to be honest. His hand and fingers did the trick of training and relaxing me. this "Training" usually occurred during very heavy cunnilingus sessions, so we were both feeling very good and relaxed about the whole endeavor.
Also, we found if I orgasmed at least once or twice BEFORE attempting any anal penetration it was much easier. I was relaxed, and at that point, pretty much anything
would have been OK with me. Also, being well lubed, as you know, is very important. (However, we found TOO much lube and things just get messy. You have to find the right amount and the right lube for you. I like the lube in about 1/4 to a half a vial of Astroglide Anal Shooters.) We also found that if I had the very familiar sensation of vaginal penetration DURING anal sex, it was not only easier, but I was more relaxed and aroused. We found double penetration is actually preferable for our needs to simple anal penetration alone. We usually use the Fun Factory Boss Lady for this, either still or with the vibration turned on, depending on what My Man and I are in the mood for. We've also tried anal sex with the Wahl Massager on my clit, and it is really a fun sensation. It takes about every hand on deck, but it is worth the work!
The first time we actually achieved anal intercourse, with no discomfort and a lot of arousal on both ends, he was so caring and sweet and encouraging. We had tried
it once before (without enough conditioning and training) and it hurt, and I bled (I didn't even bleed the first time I had PIV sex) but this second time he just kept telling me how much he loved me, and how sweet it was and what a Good Girl I was and it was wonderful.
Now, we play this way frequently, and the plugs, at least for me, came after learning with fingers hands and penis.
Now, quite a while later, I still don't like large toys, taken anally, I prefer small ones, as I like the full feeling, but not too much stretch unless we're having actual sex. (although have no problem with his penis, there's a difference, at least to me, in living human flesh and even the best silicone) I actually like the small Plug of Lust or a set of beads during oral, but usually want them removed before I come, as that what works for me most of the time.
I, personally, never wear a butt plug unless we are having sex. I find the sensation TOO sexual and can't just sit around with something in my butt, but everyone is different, and you'll find what works for you.
Every body is different. Take it slowly. Stop if it hurts. Allow yourself to relax and enjoy the sensations, and most likely you will eventually achieve whatever level of anal play you and your partner desire.
Gentle hugs and good luck.