HIDDEN IN THE SHADOWS- kill 10 fully cloaked spys while they are crossing your line of stickies
MID-AID MASSACRE-kill 20 enemies while there are in the air (jumping from any class, and other demos in the air along with soldiers rocket jumping) with your granade launcher.
FYI I BE A DEMO!-KIll a spy that is being healed by your medic.
I HAD ME GOOD EYE ON YE- kill 50 disguised Spys, or spys that have just cloaked.
OH THERE GONNA HAVE TO GLUE YOU BACK TOGETHER..IN HELL-kill all enemies on a control point that is X6 or more.
KABOOOOM- kill 2 or more enemies with one crit nade, and after they die give them a screenshot of you taunting them. 
NEVER SAW ME COMIN- sticky jump behind an enemy, and kill him with out him even turning around.(crits are more for this one)
BUZZIN-Kill 5 enemies in one life with your bottle
IF I HADN'T BEEN DRUNK- Kill 10 enemies in one life with your bottle
ME BOTTLE OF SCRUMPY-kill 20 enemies in one life with your bottle
NEVER LOOK BETTER!-KILL 30 ENEMIES IN ONE LIFE WITH YOUR BOTTLE!!!
LEEETS DO IIIITTT!!!- as soon as the set up time has ended kill an enemy with in (5 or 10?) seconds of the match starting
THE LOT OF YEEEH!!-kill an Engie and his intire set up(his sentry gun, disp. and tele) with one Clip of sticky Bombs or nades.
A PINCH- destroy total 100 buildings
JUST A SPARK-Destroy a total of 1,000 buildings
KABLEWIE!!-destroy a total of 10,000 Buildings
YA DANDIES-kill 5 enemies while there taunting
I AM FULLY(UHH!)-kill an enemie medic as soon as he is 100% ubercharged
FLYING SCOTSMAN- use your sticky bomb launcher to jump above your enemies and as soon as you land pull out your bottle to kill a total of 100 enemies
DEATH BOX- fill a room with all 8 of your stickies and as soon as a group of people walk in you detonate and kill all of them
UNHAPPY ENDING-get an enemy to chase you and as soon as he turns a corner you kill him with your nades, stickies or bottle
YOUR GONNA NEED MORE BANDAGES- CAUSE A TOTAL DAMAGE OF 100,000 POINTS (NOT KILLS)
DON'T CHASE ME BOYO!!-bounce a nade off a wall, and the same nade kills the person that is chasing you
UNTOUCHABLE-in a single uber destroy 3 sentries, 3 disp, along with there engies(the ones that are fixing the buildings)
ESCAPE PLAN B-when your about to sticky jump out of harms way! you also kill the enemy that is attacking with the same sticky that you used to get out of harms way.
WTF's A SANDWHICH?!-kill 30 heavies while they are all useing there sandwhiches to heal up.
NEVER HAD A CHANCE...-Separate a medic from his uberbuddy, as soon as there uber starts, or before they even get one kill.
Thats what i just thought of at the top of my head and there challeneging, and i want to see that alot more especially for the demo, so thats why i set the bar pretty high. so if there are any ideas from my "leeets dooo iiit" achievements reply back. or if you have any more add ons ill be more then happy to hear. so please tell me what you think!
LONG LIVE THE DEMOMAN!