When we first got Roman (at the age of 6), he was trained to only be on special dog beds around the house. We were given at least 3-4. A couple downstairs, one upstairs and then one outside. After a few months with him, we noticed how cuddly he was and decided that it wouldn't hurt to have him on our beds. It took some time to have him get used to breaking his prior rules, but he did and to this day he loves it.
I will agree that it is really uncomfortable to sleep with a dog; especially on a twin size bed. But it's worth every minute. Plus, during the winter, it's a lovely free heater! To this day (at the age of 14, soon to be 15), he sleeps on our beds and couches.