@Georgio Are the jiggle balls for yourself? Anything you’re inserting anally (sp?) should have a flared base to stop it going fully inside you. Jiggle balls don’t have this, you’d need to create something to stop it slipping in too far, they have a pull cord but that might not be enough unless theres something wide on the end of it.
Hoodlum is semi-longish and the one I’m referring to, sold by LoveHoney. But it’s double ended and thin so kind of doesn’t count to me, now. I wish I had gotten Doc Johnson Double Veined Double Headed instead though as it’s a bit longer.
The reason I started with Double Dildos for depth is the exact answer to your question. Safety and not hurting myself internally. Double’s are great to start depth play with with due to the slender nature which is what is needed to pop the inner sigmoid curve “turn” by making it less of a 90 curve angle and more 75 or less, more like a left arc rather than a hard left hand turn. Once you have done that you can continue with whatever size or depth for whatever reasons (within reasonable limits) that you want. With no risk of internal injury as long as you listen to your body and stretch first rather than just mercilessly ram things to begin with. Fortunately once you know your body’s limits and improve them safely you can then get mercilessly slammed relentlessly. 
Doc Johnson Dick Rambone 13.5 Inch isn’t a double ended dildo and is much more massive as a result and would be considered Large and is the next curve progression toy I used. It does take time and understanding of the things to avoid/general anatomy etc to enjoy (safely). But it’s so worth it. The ridiculously longer range end of dildos are over 26” but have to be more flexible to navigate the curvature of deeper smaller intestine’s anatomy.
At any rate Deep depth play with girth are fortunately what both my GF and I enjoy when she’s pegging me. Unless she’s prostate milking me. Our current favorite is the Intimidator .I have longer more girthy ones from competitors but I’m not quite at the point of being pegged by them just yet. Depth is totally worth exploring. It’s a feeling unlike any other I’ve experienced from being pegged without just aiming for prostate orgasms. I get both types though with depth play with enough girth. I find girthy depth extremely…. pleasurable in a unique way, as I stay extremely erect, have anal orgasms as well as prostate ones incidentally as well.
Hope this helped address your concerns and maybe encouraged you to look into something new.
Guys you are amazing, as much as I’d love to there are too many of you to reply to individually. You all have given such great tips n advice. Ironically the day I posted this I had a few drinks, took a deep breath n went for it. It was amazing once got settled inside. It is a prostate massager but bigger than I already had. I don’t like warming up with my cock cause I prefer to have a hands free orgasm when going anal. I relaxed, listening to an erotic podcast, got very aroused n slipped it in. Left it in a for a bit before I turned it on. Was fantastic, strong vibrations in the right place. Lots of pre cum but didn’t hit the point of full orgasm, bloody batteries ran out, so frustrating as I think I would have. Have it on charge now for another go later. Can’t wait. Will defo keep moving up in size and power gradually
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