Sistergrin,
Congratulations on your new little boy
Firstly, i would like to say you are DEFINATELY NOT A FAILURE, these times are really difficult as your hormone levels are everywhere and you and your baby have a task at hand - breastfeeding is an art that both of you have to learn. YOU WILL SUCCEED it will just take time.
Many of the other mums have giving great advice regarding expressing before trying to latch him on - as it would be very difficult to latch him on, and for him to latch on, when your breasts are so firm. You must express enough for your breasts to be comfortable and softer for latching.
Also, if he is very sleepy it is probably best to syringe feed him (using a bog standard medicine syringe from chemist - previously suggested by Pruhoohooohoooooni)-with what you have expressed. This will increase his sugar levels and make him more awake.
Regarding what the Midwife said about the flat nipples. I would recommend NOT using nipple shields - although this may help with latching, it will not solve the problem and may also lead you to future problems - reduced milk supply, dependency to it. I would suggest using Nipple Formers, these are worn between feeds and encourage the nipple to come out for easier latching. Or you could use your pump just before latching to pull your nipples out ;)
Also, remember that if your baby is not latching you will need to express a minimum of 8 times a day to stimulate your breasts enough for producing milk. All the milk expressed can be stored and used in future feeds.
Please contact your Midwife or Breastfeeding Councellor for info and help. They will be great encouragement for you.
Or you could call a Breastfeeding Helpline:
BFN: 0870 900 8787
LLL: 0845 120 2918
NCT: 0870 444 8708
Hang in there, you are doing a fantastic job. Keep us all updated.
Take Care x