Haven't had the chance to try this.>>20118932
This is definitely the case until you can get your entire head in. From that point onwards, it feels amazing.>>20103695
First off, I definitely recommend losing some weight and exercising regularly. It also helps if you haven't eaten for several hours/have an empty stomach when you're going to attempt.
I can't recommend the C-pose enough. The legs-over-head method seems intuitive for beginners, but it's a lot easier to hurt your neck or back and push yourself too far.
For the C-pose (sitting, standing, or laying and then hugging your legs to your body, so that your spine forms a "C"), it's important to realize that bending your back only gets you so far. A large part of closing the gap comes with making sure your hips are thrust forward as much as possible - engage your glutes to extend even more. It can also help push your dick forward if you cross your legs slightly and optimize the position of your balls (sometimes placing excess skin in between your legs can help keep it facing straight towards you).
The other thing is that your spine only bends so much, so to get the best results from the C-pose, you need to think about getting your torso farther backwards, away from your feet. I get the best results when sitting on a chair or sofa, extending my legs straight out and crossed, engaging my glutes to push (and rotate) my pelvis maximally forward, hooking my arms under my legs as tight as possible, and bringing my head as far back on the horizontal plane as I can by "rolling" my torso a bit. It may help to put your forehead against your quads and then use your neck and back to pull forward
Remember to breathe and take short breaks where your retain 70% of the stretch but pull back a little. It helps if you've worked out that day, if it's later in the day, or if you've taken a warm shower beforehand.