I’m at a point where my sex drive is increasing and I want to have sex / play with my dildos again but I have very tight pelvic floor muscles and find penetration painful and often impossible. I have tried using dilators in the past and they have worked temporarily until I stop using them. I go through phases of being ok with having a vagina to phases of gender dysphoria where I don’t want to think about it. Everytime I want to start having sex / playing with my dildos again I have to go through the tramatic experience of using dilators again. Not only do I find it uncomfortable and often painful, I hate anything medical and have a real aversion to using dilators because they look too medical, I shake noticably and feel sick. I am wondering if there is an alternative that is less medical looking and more sexy. I can’t use my fingers because I have sensory issues and can’t stand the feeling on my fingers. I realise that I may have just taken away the only other option available.
There are dilators available that look less medical so you could have a search around and see what you can find.
Otherwise, how small do you need to start?
This is probably the smallest toy Lovehoney have and has the benefit of vibration, which can really help the muscles relax.
But generally the anal section would be a good place to start if you are looking for things that are more toy like. A few examples:
If you like one that doesn’t vibrate, you could also add a pebble/lay on type vibe to add some vibration.
Otherwise, have a look in the Bullet section. Some might still be too big and others with be too short for full insertion but could be used around the vaginal opening which may make it easier to take a slightly larger toy after.
There’s a couple in the G Spot section namely this finger one and this much more expensive option
Feel free to ignore what I am about to say (as it is unsolicited advice) but have you considered trying to reframe how you view dilating? Making it less about your vagina and more a thing your body just needs you to do. Make it part of a routine, like something you do in the shower or when you’ve woken up, had a wee, cleaned your teeth and then dilated. If you look up the artist Hazel Mead she has done a commission with the Vaginismus Network about how to make dilating less of a chore.
Thanks @Calie. That’s really helpful. I’ll have a proper read through tomorrow and write a more decent reply then but there’s lots there for me to look into. Thank you 
About the best thing I’ve found is just to continue sticking things in there. I’m naturally tiny and very tight, and getting used to being penetrated by fingers or an object took some time. For a while, GF would put her index fingers inside me and then pull sideways to stretch. I agree that dilators feel too medical. I tried them and it wasn’t for me.
In hindsight, I think a big reason why I was so tight was lack of use. I had a thing about keeping my cherry intact for my first partner, so I didn’t put anything inside myself really until age 26. When I finally let GF do it, it hurt a lot and bled like crazy. My sister did it a long time earlier - she just slipped a toy inside herself and it was no trouble.
The vagina is a mass of muscles…the more it gets used, the better it works. Its meant to push out babies, after all. I’ve worked on mine for enough years that if I’m relaxed, I can comfortably take GF’s hand inside me. I spent 12 long months working to achieve that, and I felt pretty good when GF finally got wrist-deep in me. And while I prefer anal with my husband, we get plenty of practice at PIV too…
I really feel for you @Kitty-Cat01 and the problems you are having. I think @Calie suggestions are spot on and you should seriously look into them. Good luck in finding a solution. Big hugs all around. 
I’m a bit awkward because I find very small things feel sharp and painful, when i tried dilators in the past, i skipped the smallest size and tried the 2nd. To answer the question, something bigger than one finger but definitely smaller than two.
The anal toy idea is a good suggestion, they tend to be smaller and bullets might work too. I’ll probably avoid beaded toys for now because the texture might not help but a smooth anal toy might work. The g-spot finger vibrators look like a good 2nd step but possibly slightly too big for a first step.
This is a good point and probably sums up the problem. I’ve tried to think about it differently which is the reason I now feel like i might be ready to try again but it’s really challenging. I’ve tried counselling, sex therapy and CBT for phobias but haven’t managed to improve my mental association. I think of it as a phobia, it’s a phobia of medical procedures combined with a phobia of pregnancy etc and then the added complication of gender dysphoria. I think i could get my head around sex with my husband by thinking of it differently but trying to treat my vaginismus seems to come under the medical category so feels very different. It’s very frustrating! I guess the only way i can describe how i feel is like i’ve been violated in some way even though i’m doing it myself. Sorry, i went a bit off at a tangent there! I’ll definitely look up the artist you mentioned, that could be helpful.
Thanks again for all the thought and effort you’ve put into this @Calie 
Thanks @steve19 I will do x Thanks for the hug too, it feels much needed at the moment!
Thanks @awkward-yet-sweet, I don’t think my OH could get a finger in if he tried, it’s like hitting a wall! And he’s too scared to try. I think you have a point about age, I never masturbated until i was in my 20s and had a really negative upbringing where sex was wrong and it wasn’t something i wanted anything to do with. For some reason i thought i didn’t have a vagina and my clitoris was just a miniature version of a penis which for some reason didn’t grow. I think i just mentally blocked it out so i didn’t have to accept what i was taught about the purpose of my body (to have babies) at school. To me, the ability to have children didn’t apply to me and when i eventually realised that it did, i was horrified.
@Kitty-Cat01 A lot of getting things loose enough to work is just getting in there and doing it. Even if it hurts. The reward later is worth it.
I guess I was…lucky?..to have a GF who was insistent. She pushed past my boundaries and worked on me pretty hard. There were some times where I struggled and complained and got penetrated anyways. If she evaluated my body and determined that I needed to cum, then she was going to play with me until I did.