Anyone else?
Ben has started to use "I'm hurting" as a way of getting what he wants. I hate it because a big part of me knows that he is not hurt and that he is just trying to get his way but this tiny little part of me always falls for it and wonders if he is really hurting 
When he is trying to avoid sleep he says his belly is hurting. This morning his feet were hurting when I tried to put socks on him and then basically everything was hurting and we went from fully dressed to him pulling off his pants, socks AND underwear and then sprawling out on the floor with only a shirt on because all the rest of his clothes were hurting. He will only wear "comfy" pants because every other kind of pants hurts. Every morning his socks and shoes hurt his feet.
I am just at a loss. I need to get him to stop using the hurting tactic because honestly it is creating a boy who cried wolf situation and I don't know whether to believe him or not when he says he is hurting.
ETA: For the record, all of his clothes and his shoes fit him properly, nothing is too small.
Re: Anyone else?
Sometimes I'll give Nate a little bit of medicine to help him feel better, even if I think he's making it up. Last night he kept telling me his feet hurt at bedtime. I figured he was either being silly, or maybe his feet are growing and were hurting some. So I gave him about half a dose of ibuprofen. I figure that the placebo effect is worth it, and he feels like I'm listening and taking him seriously. I wouldn't feel comfortable doing that every day, but on rare occasions, I don't think it's a big deal if he takes a little medicine, even if he doesn't necessarily need it.
As for socks and shoes, pants, etc, have you tried giving him the option of going without? That's my default with Nate and it usually gets him to put his pants/shoes/etc on. I pretty much say "Do you want to wear socks and shoes, or do you want to go barefoot? You can go barefoot, but it's cold outside and your feet will get cold," or "Do you want to wear pants to daycare, or go in your underpants? Your legs will be cold if you don't wear any pants." I'm not saying that this ends the fight, but it usually helps him to realize that he pretty much as to wear appropriate clothes outside. I'll admit that I've let him get in the car without socks and shoes on too. I know his feet get cold the second they touch the garage floor, so by the time he gets in his carseat, he's asking for socks and shoes.
I hope I don't sound too mean! :P
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You don't sound mean at all
Clearly I need to use logic. Obviously we can't leave with no underwear on, but tomorrow he might leave the house without socks just so that he can see why he needs them.
This all sort of started when he tasted medicine that he liked and then he would make something up to hurt so he could try to get that medicine. I will give in sometimes if there is a possibility he is really hurting but like you said, I don't want to give him medicine every day. I thought about buying Smarties lol so it looks like medicine but isn't. I have also bribed him with other things like fruit snacks if we absolutely HAVE to get in the car like 5 minutes ago. I hate it and it is getting out of control because at that point I know I am only making the issue worse but I can't be late every single day either.
Yes, we are dealing with this at our house too. Jocelyn either has a headache, back ache or stomach ache 50% of the time and she begs for medicine. When Cameron had an ear ache she came with me to the doctor and told him she had a broken elbow. Part of it is wanting attention, she she's Cam takes reflux medicine and also took medicine when he had an ear ache so she asks for it to. I put water in a medicine dropper and give it to her, or I've given her infant gas drops to pretend like it is medicine so she will stop asking for some.
It is for sure a stall tactic/and a cry for attention. Most of the time if I tell her I will have to take her to the emergency room and a doctor will have to examine her, that clears it right up! It is frustrating, but also I don't want to ignore it because sometimes I know she is telling the truth. The belly ache complaint has turned into major diarrhea before, so I am also cautious when she says that. Just figure out what he really wants and that should help!
Caleb often says "I hurt myself", "I need something to make me feel better", or covers his eyes and "hides" as a stall tactic. I find it really annoying, and know 95% of the time he knows he's being deceptive.
For what Ben is doing, I would try two things. First, tell him if he's sick/hurt/etc that he can't do XX. "Ben if you're hurt, you'll have to stay in bed all day & not have breakfast etc." Put him in his bed, close the door & walk out. If he wants to get out of bed, he'll need to get dressed and cooperate. I imagine he'll quickly see you mean business.
I would also try consequences, if you don't get dressed the first time I ask - you will go in time out/lose your favorite toy/etc. Tell him you want him to be comfortable and know these clothes will keep him warm etc.
Sometimes, its not worth a fight. If Caleb wants to wear his crocs today, as long as I don't have an absolute reason for him to wear sneakers, I let him. I let him make choices about getting dressed. Pick the pants you want to wear, what color shirt do you want today. Sometimes its not what I would choose him to wear, but it works!