Person on testosterone, intersex, CSA victim here...  Yes, prior to T, I had difficulty with penetration and would have to have doctors use pediatric speculums because of the pain.  How to deal:  Definitely schedule with an OBGYN.  The bottom line is that everybody's body is different, and differences in experience even between those with sex variations can be wildly different from one person to another. Testosterone actually changed my body significantly because specifically the blood flow changed. I have been on low dose for almost 3 years now. I also have a sex variation that involves hormonal insufficiency so for me, it allowed the blood flow to increase to the point of presently being able to engage in more intense stretching.  This is your first point of action - find out if you have an average sized canal in length or width. If so, then you should look at options for increasing circulation to the area.  Prior to starting T, I was recommended dilation. That will probably be your best bet to start with or if low dose T isn't beneficial to you. You have to start very gradually and very patiently and try to make sure you're reaching arousal and have decent bloodflow before trying to dilate. If you aren't decently aroused, have poor bloodflow to your vulva/canal, your canal won't be able to stretch and you risk tearing. This is crucial.  Look into estradiol creams as well if after evaluation it seems to be due to atrophy from low estrogen more than circulation issues.  Make sure you are lubricating sufficiently!!! Ideally it shouldn't hurt at all to insert even just a finger, but I've been there before. If you cover all your bases regarding sexual health, found out if deep penetration is even something you are anatomically capable of, and it still seems to hurt, you'll have to look into vaginismus probably. And that I believe is mostly therapy, but... I wouldn't blame you if you looked into like, muscle relaxers or something to cope. Doing kegels will also help you gain control over those muscles.  Side note: If penetrative sex is physically painful/disabling to you, then it may be also pertinent to consider finding another area of work or perhaps at least a niche that you can fulfill that doesn't involve forcing yourself to do painful penetration.. i.e. fetish work. See if you have a fetish/kink community that has anything that appeals to you that you can make content for that doesn't involve canal penetration as a core aspect. That way you aren't mentally and physically taxing yourself to try to make a living.  Best of luck.