this issue is exactly what I've been going through, but I've felt that once I past the 2 months it's gotten better, maybe from my technique that I now use. This is about the third time I've changed my technique just to make it possible! pain sucks.
Set everything up around you, spread your legs just enough to get the dilator in without touching your legs. I know that time is of the essence for you but clear at least a total of two hours for set-up, dilation and clean up. Lay still with your eyes closed for at least 5-10mins.. don't flex leg muscles etc.
Cover stent with lube up to five inches and stand up on bedside table, put lube on the index finger of the hand with your glove on (non-writing hand) and put about 3-6 finger fulls of lube in the opening.. each time go further in and push a finger inside and pull up moving from side to side, rest, pull up and move from side to side... the longer you do this the easier it will be to insert.
I grab the stent and add a second layer of lube to the first three inches, then hold it down ready and with the other hand (glove hand) put my finger back inside to pull up one last time.. then as you pull the finger out go straight in with the stent ...slloowwllyyyy....... it will only go in maybe an inch or two and feel like it pushes the muscle inside... rest it as far as you can handle and just hold it there for five mins. IT will slowly stretch the skin over the stent a little, you can pull it out a tiny bit to feel the skin pull back a little once it's over the stent. After five mins pull out and push the lube back down to the tip of the stent.
Re-insert as quickly as possible and you should get to around three-five inches, at three inches hold it for five mins and then pull it out slightly and rotate gently to begin with, if that hurts just pull out push down the lube and try again. Rotating downward and up around the sides is most comfortable, in the shape of a smile then progressing to a full circle. Don't just go in one direction but every two-three circles go the opposite direction, otherwise it feels like you are twisting the skin around in side.
By the time you get to five inches pull out and push the lube back down the stent, I wipe the drips from below with my finger and put them back on the stent. I use an alcohol free wipe in that area before starting so it's clean. saves on lube, if there are still dry spots then I add more as needed. having what seems like two layers worth of lube on really helps!
I lube the stent now to six and a quart and push back in, you wanna re-lube as quick as possible as lube will flow out of the cavity and you don't want that, keep it in there! also it should go in quite easy by now... it takes me 30 mins to get to six inches.
I don't lube up the stent completely at first because it's hard to hold and reach down with it, having that extra inch to hold for the first 30mins stops you tensing up as much. When I pull it out I hold it between my fingers like a cigarette and just as it reaches the end I twist my fingers around so I can grab it as it comes out!
The last inch is nasty but once at six inches I rest with it in for around five mins, pull out slightly rotate and push in and try and get more depth. The last inch can take between 15-30mins.. re-lubing can make you go from six and a quart back to six but you get the quart and more back quicker than the first time. I re-lube quite a bit during the last inch but it helps so much, it takes the burning feeling away which is the majority of the pain. The resting without applying pressure for five minutes helps to stretch the skin.. time helps here the more time it's sitting there stretching the easier it gets. So if it still hurts hold it in where ever it is for longer until it stretches/adapts.
Once I finally get to seven I hold for five mins and then pull out, re-lube/back in. when working up to full depth I don't do the 15 secs of hold and 15 secs of rotate but more like 30-60secs of hold and 5-10 secs of rotate. Once I get to seven I will go the standard 15sec and 15sec. but as the lube dries towards the end of the 15mins of full depth I go back to closer to a min of hold. Once at full depth it's comfortable enough to really give it a good wide rotate as well compared to time reaching depth I only do gentle circles.
I've read that douching with just warm water before a session can help battle dryness. Also if you have extra time to spare then do an extra 15mins at full depth, I extend the hold out to around 2mins with 15sec rotate for that. Also I don't douche after my night time dilation, I figure it will be a little lubey still in the morning but not sure if it's safe so yeah.. but I think it helps

You are a week behind me and I feel like last week was my toughest period so far, the last week has been better. So if we are as similar as I think then it will get better during next week!

key words: RE-LUBE!