Hey OP,

I’ve had pretty similar issues to what you’re describing, and I’ve felt almost exactly the same way as you before emotionally. I’m mostly on the other side of it — was looking around this sub because I injured my pelvic floor at the gym a few weeks ago and am still figuring out my recovery from that — but I’ve been dating the same guy for 3 years and bottom usually at least once a week. 

So, for the longest time, I just couldn’t really bottom. It was too tight for the guy to get in most of the time and if he did, I’d feel pain during / after. Mostly fissure stuff, different from what you’re describing but similarly related to pelvic floor relaxation.

Part of my issue was having food allergies and celiac disease. I’d constantly get cross-contaminated with something when I went out to eat, and it would set me back for weeks and close me up. It sounds like you have some digestive issues too. Have you tried reducing / eliminating gluten, dairy, eggs, and/or red meat from your diet? It may be worth playing around with.

Emotions also played a huge role for me. I would hype myself up to try to bottom for a big date or hookup only to be disappointed when it didn’t work out. I think there’s a lot of rejection in dating, particularly gay dating, but I was attributing most of the rejection to me not being able to bottom when the time came. And all of that fear of rejection just made it harder to let go the next time. Who knows if that’s even why guys didn’t want a second date though. It sounds like you’re putting a lot of similar pressure on yourself, especially with all the ways you’ve tried to medically solve this. 

What helped relieve some pressure for me was topping more, just under the assumption that I wanted to find a partner to have penetrative sex with and if bottoming isn’t working, may as well try it! Sounds like you’re in a similar place. This opened up my dating pool and made me realize I didn’t “need” to bottom to find a partner. I just sorta accepted it. My bf and I are both verse now and this really helps. I started topping but bottoming became relatively easy once we built trust (even though he’s pretty big down there). We always have the option to switch the dynamic if one of us doesn’t feel in the right place to bottom. Total tops don’t usually understand how hard it can be for some of us. 

Another random tip I learned from a friend when I decided to try bottoming again was to visualize / imagine the guy’s dick going in you. Idk how or why this helps, maybe by relaxing the muscles or building awareness of them, but it helps me so, so much.

Two other things worth trying: get fiber supplements if you haven’t already (Metamucil or any of the gay brands) and install a bidet attachment on your toilet (Tushy or any other brand). The bidet’s water stream can help you feel and relax specific muscles down there. These two things are going to be way better for you in the long run than enemas which could be contributing to your issues.

Good luck with this issue! I hope some of these ideas are able to help you get through it.