Big Boy Bed

We have made several attempts to gt Kaden in a big boy bed over the past year. I think we started trying when he was about 18 months. He has one of those drop side cribs and we took the drop side rail off and had it set up as a day bed toddler bed. I was nervous about him falling off the side so we put up a crib rail which was pretty much the whole side of the bed so it was basically a crib again. For his first night in that bed, he went down really easy and stayed in it all night long. I was worried the whole night and didn't sleep in fear that he was either going to fall out somehow even with the rail or gt caught in between the rail and his bed or wake up and be scared because it was ll new to him. None of which he did. I must have checked on him at least 15 times that night. Needless to say after no sleep, he went back into the crib the next day. We waited several more months and tried again. This time it was a spur of the moment decision I had made while Kevin was still at work. When Kevin got home and saw the side rail off again he questioned me and said, "Do you really think he is ready this time?" I said oh yes, all the other babies are in big beds, ours can do it. Well bedtime came and we did our regular routine of Bath, a little bit of calm play time, brushing his teeth, book, and then prayers, and then bedtime. He got up several times and we had to keep putting him in back in. After about 30 minutes of that, I decided to get IN the bed with him. I laid there next to him until he finally fell asleep, I then was able to sneak out of his room and he slept all through the night in his bed. I told Kevin that I was not going to be one of those parents who has to sleep in their child's bed for half the night or have their child sleep with them in the bed before putting them in their own bed. I just don't want my child relying on me to be able to go to sleep a night. Kaden has never had a problem with bedtime while being in his crib and I don't want to start. Well we ended up putting him back in his crib yet again after me having to help him sleep in his big bed.

Here we are at 24 months old and we think its about time to make the switch once more and hopefully being the last time. Kaden is getting so big and he ends up sideways in his crib all scrunched up because he no longer fits. We borrowed a twin box springs and mattress from Kevin's parents house and set them on the floor. I went to Target and bought the bed set I have been dying to buy ever since he was 18 months old and trying the bi boy bed for the first time. It is a really nice quilt set with cars and truck on it. Kaden loves cars so I thought this would make the transition a little better. I was hoping he would think having cars all over his bed was cool and would make him want to be in it. We put the rail up between the box springs and the mattress and that first night we did our routine and put him in his bed. He rolled over and went to sleep, easy as that! I was amazed at how good actually GREAT he did. I checked on him twice and he had not moved an inch the whole time. The next morning he slept until about 8:15 which is longer then his 7:30 time he usually wakes up at. That morning we went to church and out to lunch with my dad and step mom and then made a tip to Lowes to pass a little bit of time and get Kaden a little more tired in hopes that nap time would go just as good as the night before. We get home and get Kaden ready for his nap and put him in his bed and walk out and as soon as we got to his door, he is up out of the bed screaming and crying behind us. So we put him back in his bed and told him it was nap time and he needed to stay in bed. We did this for probably close to 2 hours without any sign of him cooperating. The crying never let up and he was not going to sleep. It broke my heart to see him crying as hard as he was. Just the belly aching kind of cry. We were cleaning out or garage that day and my mom was coming over to take Kaden out of the house so we could get that done. I just told her to go ahead and take him without him going down for a nap. I thought after he comes back from being out and paying he should be really tired and we could try it again. They got back close to 4 and it was the same thing as before. The tears started flowing and the belly acing and getting out of the bed every single time we would get to his door. Needless to say, he didn't take a nap that day. We went to my in laws for a cook out that night and came home which of course on the way home Kaden falls asleep. We decided we would skip bath time and the bedtime routine and just undress him and put him to bed. Well he woke up while we were undressing him (which he never does usually) and he realized what we were doing and he started to cry just like he did at his nap time. Since he was up already we started with his bed time routine. A little after 9 I went to feed Karsyn a bottle and Kevin attempted to put Kaden to bed again. I came out from feeding Karsyn and Kaden was in his bed, no crying, no getting out and on his way to sleep. Either he was way too tired to fight anymore at this point, or bed time is just easier then nap time and since it is dark he knows it is time to sleep. Well here we are today and nap time rolls around and just like yesterday he throws a fit. After an hour of trying, I laid down with him like I did several months ago and waited until he was asleep to creep out! He slept of about an hour and woke up crying and running out of his room!  I don't know what to do or how to handle this? Is he just not ready or this transition yet? Am I doing something wrong? If anyone has any suggestions or tips I would appreciate them!!

Kaden in his big boy bed on the first night! A success!