Hi PollyIndia,
I posted about a year ago with similar issues - I was crying and swearing with every feed, each one got worse, but I was desperate to bf him (he's my 3rd, managed the other two despite similar issues with DC1).
DS2 was very windy (unlike others), clicky when feeding, terrible latch, poor tongue protrusion (I know this isn't definitely TT), and all the horrid nipple issues (lipstick shaped, cracked, bleeding etc). The feeding consultant looked horrified at them after 5 days. TT was mentioned as a possibility, but no-one seemed certain, and I looked into it here a lot. Tried nipple sheilds and just couldn't get the hang of them, plus DS couldn't get milk out of them and would get frustrated.
We did this (and it worked): I stopped feeding and pumped every 2 hrs (one gap of 3 hrs, others all 2 hrs). DS had one formula feed to start me off, then the rest was expressed milk. It was a pain, feeding with bottle, pumping, washing bottles etc, but it let me heal. I used lansinoh and moist would healing, and they were better in a few days. Pumping was much less painful. I was told you need to keep the frequency high (not the volume so much) to ensure you have enough milk (8-12 times in 24 hrs). Not fun to set the alarm to pump in the night every few hours!
When I restarted feeding (4 days break) I was quite terrified, but watched a lot of the video clips of positioning (can't remember the links, but they were from mumsnet threads - possibly milkmatters and kellymom, plus another american one), and really tried to encourage a better latch, using different positions to vary the stress on me.
I found that as he got bigger the pain reduced, as his mouth grew it was able to do a slightly better latch.
I wasn't sure whether to snip or not, and looked into it and decided if he was able to feed without actual pain to me, or problems for him (colic, distress, frustration, weight gain, wet nappies etc.) then I wouldn't bother, and monitor for problems with solids or speech later.
It was tricky and uncomfortable when I restarted, but each feed reduced in discomfort fairly quickly, and I never got cracked/bleeding nipples again, I think this was due to a better latch. By 4 - 6 weeks it was fairly easy, and pain free. Oh, and I realised my just carrying on with feeding when it hurt had led to worse cracks, so I was prepared to stop and express if I got hurt again.
I don't love bfing, but never have, but he has thrived on it, and at 1 yr he is still going strong (unfortunately mostly at night), and it has been what I wanted - convenient, cheap, a balm for all ills and not required the hassle of remembering formula/ cleaning bottles. He is thriving developmentally, is very very active, took well to solids, no problems with lumps, and seems to be making appropriate sounds for his age.
I really hope you get to heal over the weekend, and that when you restart things are easier - the videos and all the advice helps you through feeding. I completely agree with you about being worse than labour, and nipples bleeding glass is exactly it! Really, really good luck.