This is a great and potentially very helpful thread! To date, I have tried out a few random jelly sleeves, as well as the Tenga Air Cushion Cup, the Tenga Flip Hole, the Fleshlight STU Mouth, and the Tera’s Ultra Erotic Love Doll.
Let me start this off by saying that none of these have felt like the vagina of a real living and breathing human woman, though a few of these did feel really amazing. My epic review of the Tera Patrick Doll will hopefully go up on EF tonight, as it is finally finished, so I won't go into the details of how that doll feels.
To me, all of the various jelly sleeves that I tried only felt ok. I used them all one time and that was about it. My experience with the Tenga Air Cushion was similar, and since this cup was designed to be a one-time-use disposable masturbator, I never used it again either.
So... now we are getting to the good stuff! The Fleshlight and the Tenga Flip Hole are both fucking awesome! Yes it’s true, they do not feel like a woman, but who cares? I do plan on eventually writing reviews for both of these when I get some free time; but trust me, they are both masturbatorically fantastico!
I bought both the Fleshlight and the Flip Hole within the last few weeks. I have used each a few times; and though they do have some very significant differences, I still cannot decide which one I like better. As for both of these toys - yes your penis will be able to tell it’s not a woman, but trust me - it won’t care!
I know that this information is not very helpful on the topic of trying to find a male toy that feels like a woman, but I figured relating my experiences may be helpful if you’re just looking for something that feels really good.